Cyclopropylamine → 2-(cyclopropylamino)-N-methyl-3-nitrobenzamide

HRID 2036572

반응식

HRID 2036572 반응식
Br[C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([NH:6][CH3:7])=[O:5].[CH:15]1([NH2:18])[CH2:17][CH2:16]1>C1COCC1.CCOC(C)=O>[CH:15]1([NH:18][C:2]2[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][CH:9]=[CH:8][C:3]=2[C:4]([NH:6][CH3:7])=[O:5])[CH2:17][CH2:16]1

참가 물질

5

반응물 2

HCID 69828CyclopropylamineHCID 674334472-bromo-N-methyl-3-nitrobenzamide

생성물 1

HCID 584592352-(cyclopropylamino)-N-methyl-3-nitrobenzamide

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

반응 조건

온도
60 °C

실험 절차

A mixture of 2-bromo-N-methyl-3-nitrobenzamide (830 mg, 3.20 mmol), cyclopropanamine (666 μL, 9.61 mmol) in THF (10 mL) under N2 was heated at 60° C. for 18 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 a silica gel column using DCM-EtOAc (1:1) as eluent to give 2-(cyclopropylamino)-N-methyl-3-nitrobenzamide: 1H NMR (400 MHz, DMSO-d6) δ 8.54-8.47 (m, 2H), 7.95 (dd, J=8, 4 Hz, 1H), 7.64 (dd, J=8, 4 Hz, 1H), 6.77 (dd, J=8, 4 Hz, 1H), 2.76 (d, J=8 Hz, 3H), 2.68-2.62 (m, 1H), 0.67-0.60 (m, 2H), 0.44-0.40 (m, 2H); LC-MS (ESI) m/z 236.1 [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 a silica gel column

출처 및 근거

ORD 기록
ord-2bb29b91667e473296d380066b6d510d
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08575183B2

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