N,N-Dimethylaniline → 3-Benzoylamino-2-hydroxy-benzoic acid methyl ester

HRID 1589856Notes

Reaction equation

HRID 1589856 reaction equation
[NH2:1][C:2]1[C:3]([OH:12])=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[C:13](Cl)(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.CN(C)C1C=CC=CC=1>C1(C)C=CC=CC=1>[C:13]([NH:1][C:2]1[C:3]([OH:12])=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6])(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 949N,N-DimethylanilineHCID 7412Benzoyl chlorideHCID 12782444Methyl 3-amino-2-hydroxybenzoate

Product 1

HCID 199399203-Benzoylamino-2-hydroxy-benzoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

20 mmol of methyl 3-amino-2-hydroxy-benzoate were stirred at room temperature in toluene with 20 mmol of benzoyl chloride for 4 hours with the addition of dimethylaniline, the mixture was concentrated and the residue was recrystallized from EtOH. M.p.: 105° C.

Workup

  1. concentrationthe mixture was concentrated
  2. customthe residue was recrystallized from EtOH

Sources & evidence

ORD record
ord-6c3f8989d9434c8b8bb72b9303d58556
Source dataset
uspto-grants-1993_04
Patent number
US05200420

Reaction notes

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