3,5-Dimethylbenzamide → 2-hydroxy-N-(3,5-dimethylbenzoyl)glycine

HRID 1600572Notes

Reaction equation

HRID 1600572 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([CH3:11])[CH:10]=1)[C:5]([NH2:7])=[O:6].O.[C:13]([OH:17])(=[O:16])[CH:14]=[O:15]>CC(C)=O>[OH:15][CH:14]([C:13]([OH:17])=[O:16])[NH:7][C:5](=[O:6])[C:4]1[CH:8]=[C:9]([CH3:11])[CH:10]=[C:2]([CH3:1])[CH:3]=1

Participants

4

Reactant 2

HCID 3194853,5-DimethylbenzamideHCID 15620607Glyoxylic acid, monohydrate

Product 1

HCID 218300622-hydroxy-N-(3,5-dimethylbenzoyl)glycine

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 3,5-dimethylbenzamide (22.6 g, 0.15 mol) and glyoxylic acid monohydrate (15.3 g, 0.17 mol) in acetone (120 ml) is heated under nitrogen atmosphere at reflux for 6 h. The solvent is evaporated in vacuo to give 2-hydroxy-N-(3,5-dimethylbenzoyl)glycine. To a solution of 2-hydroxy-N-(3,5-dimethylbenzoyl)glycine in methanol (350 ml) is added concentrated sulfuric acid (4.6 ml) at room temperature. The mixture is stirred for 2 days and then concentrated in vacuo. The residue is diluted with ethyl acetate, washed with two portions of saturated sodium bicarbonate solution and with two portions of brine. The organic layer is dried over magnesium sulfate and concentrated in vacuo to give 2-methoxy-N-(3,5-dimethyl benzoyl)glycine methyl ester.

Workup

  1. temperatureis heated under nitrogen atmosphere
  2. temperatureat reflux for 6 h
  3. customThe solvent is evaporated in vacuo

Sources & evidence

ORD record
ord-13be964e72f04b698de14d31de3fbc21
Source dataset
uspto-grants-1999_11
Patent number
US05977075

Reaction notes

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