Benzoic Acid → HCID 59625820, compound

HRID 2365288Notes

Reaction equation

HRID 2365288 reaction equation
[NH2:1][C:2]1[C:11]([NH2:12])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[C:13](O)(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl.CN(C1C=CN=CC=1)C>[NH2:12][C:11]1[C:2]([NH:1][C:13](=[O:20])[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:3]([CH:8]=[CH:9][CH:10]=1)[C:4]([O:6][CH3:7])=[O:5]

Participants

6

Reactant 3

HCID 243Benzoic AcidHCID 10868DicyclohexylcarbodiimideHCID 5718252,3-Diaminobenzoic acid methyl ester

Product 1

HCID 59625820HCID 59625820, compoundYield 27.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 500 mg (3.0 mmol) of methyl 2,3-diaminobenzoate 9w and 730 mg (6.0 mmol) of benzoic acid 9x in 8 mL of CH2Cl2 was added 620 mg (3.0 mmol) of dicyclohexylcarbodiimide (DCC) and 4 mg (0.033 mmol) of DMAP. The reaction was stirred overnight and the solid was filtered off. The solid was purified by flash column chromoatography (silica gel, 10-30% gradient of EtOAc in heptanes) to give 220 mg (27%) of methyl 3-Amino-2-benzoylamino-benzoate, 9y. MS m/z (M+H+) 271.2

Workup

  1. filtrationthe solid was filtered off
  2. customThe solid was purified by flash column chromoatography (silica gel, 10-30% gradient of EtOAc in heptanes)

Sources & evidence

ORD record
ord-3954bbc9bbb345bd94ea530649aa3912
Source dataset
uspto-grants-2014_04
Patent number
US08697684B2

Reaction notes

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