Potassium Carbonate → Methyl 4-amino-3-(4-chlorocinnamylamino)benzoate

HRID 5737

Reaction equation

HRID 5737 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[NH2:12])[C:5]([O:7][CH3:8])=[O:6].C(=O)([O-])[O-].[K+].[K+].[Cl:19][C:20]1[CH:29]=[CH:28][C:23]([CH:24]=[CH:25][CH2:26]Cl)=[CH:22][CH:21]=1>CN(C)C=O>[NH2:12][C:11]1[CH:10]=[CH:9][C:4]([C:5]([O:7][CH3:8])=[O:6])=[CH:3][C:2]=1[NH:1][CH2:26][CH:25]=[CH:24][C:23]1[CH:28]=[CH:29][C:20]([Cl:19])=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1355243,5-Diamino-2-methylbenzoic acidHCID 53728250p-Chlorocinnamyl chloride

Product 1

HCID 53813638Methyl 4-amino-3-(4-chlorocinnamylamino)benzoateYield 63.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5.0 g of methyl 3,4-diaminobenzoate was dissolved in 40 ml of dimethylformamide, and to the solution were added 2.07 g of potassium carbonate and 1.87 g of p-chlorocinnamyl chloride, and reaction was carried out according to the procedure in Reference Example 40, to obtain 2.0 g of the title compound as a light brown oil.

Workup

  1. additionto the solution were added

Sources & evidence

ORD record
ord-02666c15032d4a23816abf9f01b6ac87
Source dataset
uspto-grants-1993_09
Patent number
US05245034

Linked notes

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