Water → 939999-24-3

HRID 1991431Notes

Reaction equation

HRID 1991431 reaction equation
C[O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([NH2:10])[CH:5]=1.[NH:12]([C:14]([O:16]C)=O)[NH2:13].[CH3:18][O-].[Na+].O>CO.C1(C)C=CC(S(O)(=O)=O)=CC=1>[O:16]=[C:14]1[NH:12][N:13]=[CH:18][N:10]1[C:6]1[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=1)[C:3]([OH:2])=[O:11]

Participants

7

Reactant 4

HCID 962WaterHCID 78274Benzoic acid, 3-amino-, methyl esterHCID 80519Methyl carbazateHCID 10942334Sodium Methoxide

Product 1

HCID 68691612939999-24-3Yield 47.5%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 887MethanolSolvent

Procedure

13 mmol of methyl-3-aminobenzoate were dissolved in 20 ml MeOH. 12 mmol of trimethylorthoformiate, 12 mmol methyl hydrazinocarboxylate and 50 mg of p-toluenesulfonic acid were added. The suspension was heated for 48 h to 65° C. 37 mmol of sodium methanolate were added and stirred for additional 2 h. The organic layer was reduced and water was added. The solution was acidified to pH=1 and the resulting solid filtered off to result in 5.7 mmol of product. MS(ISO): 204.2 (M−H+)

Workup

  1. temperatureThe suspension was heated for 48 h to 65° C
  2. filtrationthe resulting solid filtered off

Sources & evidence

ORD record
ord-ae5214cf6f7b4401911a1d489ffb3a16
Source dataset
uspto-grants-2010_01
Patent number
US07645776B2

Reaction notes

Loading…