1,2-Dichloroethane → 2-Amino-4-nitrobenzamide

HRID 887593Notes

Reaction equation

HRID 887593 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].C(Cl)CCl.C1C=CC2N(O)N=[N:24]C=2C=1.CCN(C(C)C)C(C)C.N>C(Cl)Cl.CO>[NH2:1][C:2]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4]([NH2:24])=[O:5]

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 222AmmoniaHCID 120764-Nitroanthranilic acidHCID 757711-HydroxybenzotriazoleHCID 81531Diisopropylethylamine

Product 1

HCID 125712312-Amino-4-nitrobenzamide

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-amino-4-nitro-benzoic acid (9.1 g, 50 mmol) in CH2Cl2 (500 mL) was added EDC (12 gram, 60 mmol), HOBt (6.8 g, 50 mmol), DIEA (12 mL), and NH3 in MeOH (2M, 40 mL). The reaction was stirred at RT for overnight, and a precipitation formed. The solid was isolated via vacuum filtration.

Workup

  1. customa precipitation
  2. customformed
  3. customThe solid was isolated via vacuum filtration

Sources & evidence

ORD record
ord-73cde8338e2240078f2a84c6fc0f398d
Source dataset
uspto-grants-2012_08
Patent number
US08247430B2

Reaction notes

Loading…