Stannous chloride dihydrate → 5-amino-2-benzylisoquinolin-1(2H)-one

HRID 749209ノート

反応式

HRID 749209 の反応式
O.O.[Sn](Cl)Cl.[CH2:6]([N:13]1[CH:22]=[CH:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][C:19]=2[N+:23]([O-])=O)[C:14]1=[O:26])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(=O)(O)[O-].[Na+]>C(O)C.O>[NH2:23][C:19]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:20]=1[CH:21]=[CH:22][N:13]([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:14]2=[O:26]

参加物

6

反応物 3

HCID 61436Stannous chloride dihydrateHCID 516892Sodium BicarbonateHCID 184445282-benzyl-5-nitroisoquinolin-1(2H)-one

生成物 1

HCID 184445335-amino-2-benzylisoquinolin-1(2H)-one収率 93.5%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒

実験手順

Tin(II) chloride dihydrate (1.21 g, 5.36 mmol) was added to a stirred solution of 2-benzyl-5-nitroisoquinolin-1(2H)-one (300 mg, 1.07 mmol) in anhydrous ethanol (20 mL). The reaction mixture was stirred at reflux for 20 h. The resulting mixture was cooled to room temperature, treated with saturated aqueous sodium bicarbonate to pH=11 and diluted with water (100 mL). The obtained mixture was extracted with ethyl acetate (3×70 mL). The combined organic fractions were dried over anhydrous Na2SO4, filtered and evaporated to give 5-amino-2-benzylisoquinolin-1(2H)-one (248 mg, 1.0 mmol, 93% yield) as an orange foam.

後処理

  1. temperatureat reflux for 20 h
  2. extractionThe obtained mixture was extracted with ethyl acetate (3×70 mL)
  3. dry with materialThe combined organic fractions were dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. customevaporated

出典と根拠

ORDレコード
ord-d50aa7129329405187ee1311c434aeaa
出典データセット
uspto-grants-2008_07
特許番号
US07402596B2

反応ノート

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