Methylamine → 2-bromo-N-methyl-3-nitrobenzamide

HRID 2036571

반응식

HRID 2036571 반응식
[Br: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].CN.O1CCCC1.C[CH2:22][N:23](C(C)C)C(C)C>CN(C=O)C.CCOC(C)=O>[Br: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]

참가 물질

7

반응물 4

HCID 6329MethylamineHCID 8028TetrahydrofuranHCID 684522-Bromo-3-nitrobenzoic acidHCID 81531Diisopropylethylamine

생성물 1

HCID 674334472-bromo-N-methyl-3-nitrobenzamide

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 2-bromo-3-nitrobenzoic acid (0.974 g, 3.96 mmol) in DMF (3 mL) was added methylamine, 2.0 m solution in tetrahydrofuran (2.97 mL, 5.94 mmol), 1,1′-dimethyltriethylamine (1.38 mL, 7.92 mmol) and (1H-benzo[d]-[1,2,3]triazol-1-yloxy)tripyrrolidin-1-ylphosphonium hexafluorophosphate(V) (2.47 g, 4.75 mmol) and the resulting mixture was stirred at rt for 2 h. The reaction mixture was diluted with EtOAc, washed with water and brine, dried over MgSO4, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel column using DCM/EtOAc-DCM (1:1) as eluent to give 2-bromo-N-methyl-3-nitrobenzamide: LC-MS (ESI) m/z 261.0 [M+H]+.

후처리

  1. washwashed with water and brine
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by column chromatography on silica gel column

출처 및 근거

ORD 기록
ord-cc6e0d8e9c424a57af304fc3f446ea1c
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08575183B2

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