Amide hydrolysis

4 real reactions from the literature, on seven-membered lactams and amides. Each scheme shows starting materials, conditions and products, with the yield and reference where the source reports them.

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1. Amide hydrolysis: caprolactam (a seven-membered lactam) with 1) aq. HCl; 2) Amberlite resin gives 6-aminohexanoic acid (the carboxylic acid).

   Amide hydrolysisOrg. Synth. Coll. Vol. 4, p. 39

2. Amide hydrolysis: caprolactam (a seven-membered lactam) with HCl, H2O; Δ gives 6-aminohexanoic acid (the carboxylic acid).

   Amide hydrolysisOrg. Synth. Coll. Vol. 2, p. 28

3. Amide hydrolysis: N-(2-bromo-4-methylphenyl)acetamide with 1) aq. HCl, Δ (amide hydrolysis); 2) NaOH gives 2-bromo-4-methylaniline.

   Amide hydrolysisOrg. Synth. Coll. Vol. 1, p. 111

4. Amide hydrolysis: an amide with HCl; H2O, Δ gives (+-)-methionine (the carboxylic acid).

   Amide hydrolysisOrg. Synth. Coll. Vol. 2, p. 384