1,2-Dichloroethane → 2-Amino-3,5-dimethylbenzamide

HRID 1041722Notes

Reaction equation

HRID 1041722 reaction equation
[NH2:1][C:2]1[C:10]([CH3:11])=[CH:9][C:8]([CH3:12])=[CH:7][C:3]=1[C:4](O)=[O:5].C1C=CC2N(O)N=[N:19]C=2C=1.C(Cl)CCl.CN>C(Cl)Cl>[NH2:1][C:2]1[C:10]([CH3:11])=[CH:9][C:8]([CH3:12])=[CH:7][C:3]=1[C:4]([NH2:19])=[O:5]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 6329MethylamineHCID 757711-HydroxybenzotriazoleHCID 2598342-Amino-3,5-dimethylbenzoic acid

Product 1

HCID 122648222-Amino-3,5-dimethylbenzamideYield 209.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2-amino-3,5-dimethyl-benzoic acid (550 mg) in DCM (30 mL) was treated with HOBt (225 mg), EDC (1280 mg), and CH3NH2 (8.5 mL, 2N in THF). The reaction mixture was stirred for 16 hours in a sealed bottle, diluted with DCM (100 mL), and washed with brine three times. The organic layer was dried (sodium sulfate), and concentrated in vacuo. The residue was purified by silica gel chromatography to provide 573 mg of 2-amino-3,5-dimethyl-benzamide: 1H NMR (300 MHz, CDCl3) δ 7.9 (s, 1H), 7.8 (s, 1H), 6.1 (bs, 1H), 5.3 (bs, 2H), 2.9 (d, 3H), 2.2 (s, 3H), 2.1 (s, 3H).

Workup

  1. washwashed with brine three times
  2. dry with materialThe organic layer was dried (sodium sulfate)
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-d547ccbcedd245069225dea4c71958f3
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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