Methylamine → 4-Bromo-N-methylbenzamide

HRID 594975Notes

Reaction equation

HRID 594975 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[CH:4][CH:3]=1.OC1C2N=N[NH:17][C:16]=2C=CC=1.C(N(C(C)C)CC)(C)C.CN>CN(C=O)C>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:17][CH3:16])=[O:7])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6329MethylamineHCID 114644-Bromobenzoic acidHCID 81531DiisopropylethylamineHCID 178418300HCID 178418300, compound

Product 1

HCID 1861134-Bromo-N-methylbenzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-bromobenzoic acid (300 mg, 1.49 mmol), hydroxybenzotriazole (1.1 eq), 1(3-dimethylaminoprpyl)-3-ethylcarbodiimide HCl (1.1 eq) and diisopropylethylamine (2 eq) in DMF (2 mL) was stirred at rt for 20 min. Methylamine (1 eq) was added and the reaction stirred at rt for 16 h then quenched with saturated aqueous sodium hydrogencarbonate solution and extracted into ethyl acetate. The organic layer was washed with brine, dried (MgSO4) and concentrated in vacuo to give 4-bromo-N-methylbenzamide. 1H NMR (d6-DMSO) δ 10.07 (s, 1H), 9.03 (s, 1H), 8.56 (s, 1H), 8.38 (s, 1H), 8.32-8.36 (m, 2H), 8.05-8.09 (m, 2H), 7.94 (s, 1H), 7.67 (s, 1H), 3.87 (s, 3H), 2.83 (d, 3H); LC-MS method B, (ES+) 349.0, RT=6.68 min.

Workup

  1. customthen quenched with saturated aqueous sodium hydrogencarbonate solution
  2. extractionextracted into ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-13ef2736cc4043e1814340f531ff39dc
Source dataset
uspto-grants-2016_01
Patent number
US09242987B2

Reaction notes

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