The hydration of nitriles to amides is one of the basic transformations in organic chemistry However, it is not generally appreciated how difficult this transformation is to carry out efficiently since amides themselves undergo further hydrolysis to the acid. We use cookies to improve your website experience. (Eluent: 40% EtOAc/hexane); 70% yield (218.2 mg); white solid; 1H NMR (500 MHz, CDCl3): δ 7.80 (s, 1H), 7.67 (d, J = 6.5 Hz, 1H), 7.50 (d, J = 7.0 Hz, 1H), 7.38 (t, J = 6.0 Hz, 1H), 6.09 (br, NH, 2H).13C NMR (125 MHz,CDCl3) δ 167.9, 135.0, 134.8, 132.0, 129.9, 127.7, 125.3. (2013) Transition Metal–Free Sodium Borohydride Promoted Controlled Hydration of Nitriles to Amides. (Eluent: 40% EtOAc/hexane); 69% yield (193.1 mg); white solid; 1H NMR (500 MHz, CDCl3): δ 7.83 (m, 2H), 7.12 (t, J = 9.0 Hz, 2H), 6.06 (br, NH, 2H).13C NMR (125 MHz, CDCl3) δ 168.3, 166.0, (d, J = 251.2 Hz), 164.0, 129.8 (d, J = 8.75 Hz), 129.7, 115.8 (d, J = 0.17 Hz), 115.6.
The residue was then purified by column chromatography (hexane/EtOAc) to get the pure product. Veisi H, Maleki B, Hameliana M, Ashrafib SS (2015) Chemoselective hydration of nitriles to amides using hydrated ionic liquid (IL) tetrabutylammonium hydroxide (TBAH) as a green catalyst. While nicotinamide and acrylamide are usually manufactured from the corresponding nitriles using metallic copper heterogeneous catalysts, … (2007), Deopura BL, Gupta B, Joshi M, Alagirusami R (2008). Ekoue-Kovi K, Wolf C (2007) Metal-Free One-Pot Oxidative Amination of Aldehydes to Amides. © 2018 Reddy NNK.
[9] In many instances the practicality of the methods have limitations such as harsh reaction conditions, high temperature, strong bases, requirement of precious metal combinations. And 2-methoxy benzonitrile subjected under standard conditions to affords corresponding amide 2q is 89%.
13C NMR (150 MHz, DMSO- d6) δ 174.9, 27.7, 22.3, 14.2.
A 20 mL round bottomed flask was charged with benzonitrile (2 mmol), sodium hydroxide (2 mmol) dissolved in isopropyl alcohol (1.0 mL).
In conclusion, we have developed an efficient protocol for the hydration of various benzonitriles to corresponding benzamides using inexpensive and commercially available base (NaOH) under very mild conditions (60 °C).The conditions also applicable to heteroaromatic nitriles and aliphatic nitriles and afford the good to excellent yields. After 90 min the mixture was removed from heat and H2O was added to precipitate a solid.
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Rao SN, Reddy NNK, Samanta S, Adimurthy S (2017) I. Li X, Li B, You J, Lan J (2013) Copper-catalysed oxidative C–H/N–H cross-coupling between formamides and amides through chelation-assisted N–H activation. (1983) Inhibitors of gastric acid secretion: antisecretory 2-pyridylurea derivatives.
Tillack A, Rudloff I, Beller M (2001) Catalytic Amination of Aldehydes to Amides, Achar TK, Mal P (2015) Radical-Induced Metal and Solvent-Free Cross-Coupling Using TBAI–TBHP: Oxidative Amidation of Aldehydes and Alcohols with.
CSIR-CSMCRI communication No. We then evaluated the hydration of heteroaromatic and aliphatic nitriles under the above optimized conditions (Table 3).
The spectra were recorded in CDCl3andDMSO-d6as a solvent.
A cobalt complex catalyzed tandem conversion of nitrile to N-methylated amide is described using a methanol and water mixture.
Using this protocol, several nitriles were directly and efficiently converted to the desired N-methylated amides. (Eluent: 40% EtOAc/hexane); 77% yield (304.9 mg); white solid; 1H NMR (600 MHz, CDCl3): δ 7.90 (d, J = 7.0 Hz, 2H), 7.67 (d, J = 7.0 Hz, 2H), 7.61 (d, J = 6.5 Hz, 2H), 7.47 (t, J = 6.5 Hz, 2H), 7.40 (t, J = 6.0 Hz, 1H), 6.11 (br, NH, 2H).13C NMR (150 MHz, DMSO-d6) δ 168.0, 143.2, 139.7, 133.6, 129.5, 128.6, 128.5, 127.4, 126.9. of NaOH as base, and 1.0 mL of IPA at 60 °C, 24h reaction time (Table 1, entry 3). [27 mg, 39%], [Patent Reference: WO2016011390, page 79, (20.2 MB)]. Initially, IPA in presence of NaOH forms iso-propoxy anion intermediate, it reacts with nitrile and produces theintermediate I which exist as keto - enol form and easily hydrolyzes to form corresponding desired amide. Compared to secondary and tertiary amides, the primary amides are important intermediates in organic synthesis and these are raw materials for the synthesis of plastics, detergents and lubricants. In electron donating groups such as -Me, -OMe, -Ph at para position of benzonitriles (2a-2d) to gives corresponding amides are excellent yields.
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