Methylamine → 3-hydroxy-N-methylbenzamide

HRID 2102371Notes

Reaction equation

HRID 2102371 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([OH:10])[CH:5]=1.[CH3:12][NH2:13]>CO>[OH:10][C:6]1[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=1)[C:3]([NH:13][CH3:12])=[O:2]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 88068Methyl 3-Hydroxybenzoate

Product 1

HCID 3537103-hydroxy-N-methylbenzamideYield 60.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3-hydroxybenzoic acid methyl ester (2.00 g, 0.0131 mol), methylamine (0.06 mol) and methanol (30 mL) was heated to 155° C. for 12 hours in a sealed tube. The solvent was removed in vacuo and the product was purified by column chromatography over silica gel using a gradient elution from 5 to 8% methanol in dichloromethane to give 1.20 g (60.4%) of 3-hydroxy-N-methylbenzamide as a yellow solid. MS [M+H] 152.2, 1H NMR (CDCl3) δ (ppm) 7.55 (s, 1H), 7.30 (d, J=7.8 Hz, 1H), 7.18 (d, J=7.5 Hz, 1H), 7.01 (m, 1H), 6.65 (b, 1H), 6.20 (b, 1H), 3.03 (d, J=4.8 Hz, 3H).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe product was purified by column chromatography over silica gel using
  3. washa gradient elution from 5 to 8% methanol in dichloromethane

Sources & evidence

ORD record
ord-91d8281ff3a94d639e912f321862a7a4
Source dataset
uspto-grants-2009_08
Patent number
US07576080B2

Reaction notes

Loading…