Dimethylformamide → Benzyl 2-amino-3-nitrobenzoate

HRID 2423243Notes

Reaction equation

HRID 2423243 reaction equation
C1(NC(=NC2CCCCC2)O[CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)CCCCC1.CN(C=O)C.[NH2:29][C:30]1[C:38]([N+:39]([O-:41])=[O:40])=[CH:37][CH:36]=[CH:35][C:31]=1[C:32]([OH:34])=[O:33]>C(OCC)(=O)C.CCCCCC>[NH2:29][C:30]1[C:38]([N+:39]([O-:41])=[O:40])=[CH:37][CH:36]=[CH:35][C:31]=1[C:32]([O:34][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:33]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 2196332-Amino-3-nitrobenzoic acidHCID 10969060Benzyl N,N'-dicyclohexylimidocarbamate

Product 1

HCID 67244884Benzyl 2-amino-3-nitrobenzoateYield 78%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Conditions

Temperature
70 °C

Procedure

Benzyl N,N′-dicyclohexylimidocarbamate (0.82 g) was added to a DMF (3 mL) solution of 2-amino-3-nitrobenzoic acid (0.36 g), followed by heating up to 70° C. and stirring for 2 hours. The reaction mixture was cooled to room temperature, then an ethyl acetate/ether (1/1) solution was poured into it, and the insoluble matter was separated by filtration. The filtrate was washed with aqueous sodium hydrogencarbonate solution and water in that order, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/1) to obtain benzyl 2-amino-3-nitrobenzoate (0.42 g). FA: 273.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customthe insoluble matter was separated by filtration
  3. washThe filtrate was washed with aqueous sodium hydrogencarbonate solution and water in that order
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-8f7c0205c42647fb89eb3c52b5ea4ae3
Source dataset
uspto-grants-2011_06
Patent number
US07960562B2

Reaction notes

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