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

HRID 2036572ノート

反応式

HRID 2036572 の反応式
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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
60 °C

実験手順

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]+.

後処理

  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

出典と根拠

ORDレコード
ord-2bb29b91667e473296d380066b6d510d
出典データセット
uspto-grants-2013_11
特許番号
US08575183B2

反応ノート

読み込み中…