Water → N-acetyl-N-(4-bromoisoquinolin-1-yl)acetamide

HRID 1922905ノート

反応式

HRID 1922905 の反応式
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([NH2:12])=[N:4][CH:3]=1.C(N([CH2:20][CH3:21])C(C)C)(C)C.[C:22](Cl)(=[O:24])[CH3:23].[OH2:26]>C(Cl)Cl>[C:22]([N:12]([C:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:2]([Br:1])=[CH:3][N:4]=1)[C:20](=[O:26])[CH3:21])(=[O:24])[CH3:23]

参加物

6

反応物 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 3118704-Bromo-1-isoquinolinamine

生成物 1

HCID 59605275N-acetyl-N-(4-bromoisoquinolin-1-yl)acetamide収率 85%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

To a solution of 4-bromoisoquinolin-1-amine (403 mg, 1.81 mmol) in methylene chloride (11 mL) at 0° C. was added N,N-diisopropylethylamine (1.57 mL, 9.03 mmol), followed by acetyl chloride (0.321 mL, 4.52 mmol) dropwise. The mixture was stirred at 0° C. for 10 min then at room temperature for 2 h. The mixture was diluted with DCM (10 mL). Water (20 mL) was added. The organic layer was separated. The aqueous solution was extracted with DCM (10 mL). The combined DCM solutions were dried (Na2SO4). After filtration and concentration, the crude was purified with flash chromatography to give the desired product (470 mg, 85%). 1H NMR (400 MHz, DMSO) δ 8.79 (s, 1H), 8.23 (d, J=8.4, 1H), 8.13 (d, J=8.4, 1H), 8.05 (t, J=7.7, 1H), 7.87 (t, J=7.6, 1H), 2.23 (s, 6H).

後処理

  1. waitat room temperature for 2 h
  2. customThe organic layer was separated
  3. extractionThe aqueous solution was extracted with DCM (10 mL)
  4. dry with materialThe combined DCM solutions were dried (Na2SO4)
  5. filtrationAfter filtration and concentration
  6. customthe crude was purified with flash chromatography

出典と根拠

ORDレコード
ord-5b0d66967ad04c65bd82509cfc9a1a0e
出典データセット
uspto-grants-2012_05
特許番号
US08173650B2

反応ノート

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