Ethanol → (R)-2-(5-Amino-6-chloro-1-oxoisoquinolin-2(1H)-yl)propyl acetate

HRID 1161275ノート

反応式

HRID 1161275 の反応式
[C:1]([O:4][CH2:5][C@H:6]([N:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([Cl:21])[C:14]=2[N+:18]([O-])=O)[C:9]1=[O:22])[CH3:7])(=[O:3])[CH3:2].C(O)C.[Cl-].[NH4+].O>[Fe].ClCCl>[C:1]([O:4][CH2:5][C@H:6]([N:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([Cl:21])[C:14]=2[NH2:18])[C:9]1=[O:22])[CH3:7])(=[O:3])[CH3:2]

参加物

7

反応物 4

HCID 702EthanolHCID 962WaterHCID 25517Ammonium ChlorideHCID 59515821(R)-2-(6-Chloro-5-nitro-1-oxoisoquinolin-2(1H)-yl)propyl acetate

生成物 1

HCID 59515650(R)-2-(5-Amino-6-chloro-1-oxoisoquinolin-2(1H)-yl)propyl acetate

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 6344Dichloromethane溶媒

反応条件

温度
85 °C

実験手順

A round bottom flask was charged with (R)-2-(6-chloro-5-nitro-1-oxoisoquinolin-2(1H)-yl)propyl acetate (160.0 mg, 0.0004927 mol) and ethanol (7 mL, 0.1 mol) and the reaction heated at 85° C. Ammonium chloride (264 mg, 0.00493 mol) in water (7 mL, 0.4 mol) was then added followed by the addition of iron (110 mg, 0.0020 mol) in two portions. The reaction was heated at that temperature for another hour. The reaction mixture was poured into dichloromethane (60 mL) and extracted. The extracts were washed with brine, dried over sodium sulfate and the solvent removed under reduced pressure to obtain the product as a colorless solid. MS m/z=295.5 (M+H).

後処理

  1. temperatureThe reaction was heated at that temperature for another hour
  2. extractionextracted
  3. washThe extracts were washed with brine
  4. dry with materialdried over sodium sulfate
  5. customthe solvent removed under reduced pressure

出典と根拠

ORDレコード
ord-c5dfcab8920747d9bead7164d90de1f6
出典データセット
uspto-grants-2010_10
特許番号
US07816371B2

反応ノート

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