1,2-Dichloroethane → 2-Amino-N-methyl-3-nitrobenzamide

HRID 724420Notes

Reaction equation

HRID 724420 reaction equation
[NH2:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].Cl.CN.C(Cl)CCl.C[CH2:22][N:23](C(C)C)C(C)C>C(Cl)Cl.CN(C=O)C>[NH2:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH:23][CH3:22])=[O:5]

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 81531DiisopropylethylamineHCID 2196332-Amino-3-nitrobenzoic acidHCID 6364545Methylamine hydrochloride

Product 1

HCID 123249782-Amino-N-methyl-3-nitrobenzamideYield 74%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

2-Amino-3-nitro-benzoic acid (1.8 g, 9.9 mmol) and methylamine hydrochloride (1.33 g, 19.8 mmol), were stirred in dry CH2Cl2 (30 ml)/DMF (5 mL) at 0° C. EDC (2.83 g, 14.8 mmol) and DIEA (4.92 mL, 27.7 mmol) were added, and the solution stirred 3 h while warming to r.t. The reaction was concentrated in vacuo and purified by silica gel chromatography (8% MeOH/CHCl3) to give 1.42 g (74%) of 2-amino-N-methyl-3-nitro-benzamide as a yellow solid. 1H NMR (300 MHz, DMSO-d6) δ 8.58 (br s, 1H), 8.23 (br s, 2H), 8.15 (dd, 1H, J=8.1, 1.8 Hz), 7.82 (dd, 1H, J=8.1, 1.8 Hz), 6.68 (t, 1H, J=8.1 Hz), 2.76 (d, 3H, J=4.5 Hz).

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. custompurified by silica gel chromatography (8% MeOH/CHCl3)

Sources & evidence

ORD record
ord-c9c7dc1dadfa4c7db6ad197bb52e7317
Source dataset
uspto-grants-2006_11
Patent number
US07141587B2

Reaction notes

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