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

HRID 1161263ノート

反応式

HRID 1161263 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]=[CH:13][C:14]=2[N+:18]([O-])=O)[C:9]1=[O:21])[CH3:7])(=[O:3])[CH3:2].C(O)C.[Cl-].[NH4+].O>[Fe]>[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]=[CH:13][C:14]=2[NH2:18])[C:9]1=[O:21])[CH3:7])(=[O:3])[CH3:2]

参加物

6

反応物 4

HCID 702EthanolHCID 962WaterHCID 25517Ammonium ChlorideHCID 59515745(R)-2-(5-Nitro-1-oxoisoquinolin-2(1H)-yl)propyl acetate

生成物 1

HCID 59515825(R)-2-(5-Amino-1-oxoisoquinolin-2(1H)-yl)propyl acetate

試薬・触媒・溶媒 1

HCID 23925Iron触媒

反応条件

温度
85 °C

実験手順

To a suspension of (R)-2-(5-nitro-1-oxoisoquinolin-2(1H)-yl)propyl acetate (5.34 g, 0.0184 mol) in ethanol (100 mL, 2 mol) was added ammonium chloride (9.840 g, 0.1840 mol) in water (100 mL, 6 mol). The reaction heated at 85° C. and iron (4.11 g, 0.0736 mol) was added in four portions 3 minutes apart. The reaction started turning dark and became completely brown. After 2 hours, the flask was removed from the oil bath and 150 ml of ethyl acetate was added in the flask. The organic layer was decanted and the aqueous layer was extracted again with ethyl acetate. The combined organic layers were dried over sodium sulfate and concentrated under reduced pressure to give a bright yellow oil.

後処理

  1. customthe flask was removed from the oil bath and 150 ml of ethyl acetate
  2. additionwas added in the flask
  3. customThe organic layer was decanted
  4. extractionthe aqueous layer was extracted again with ethyl acetate
  5. dry with materialThe combined organic layers were dried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customto give a bright yellow oil

出典と根拠

ORDレコード
ord-5303d4781d894b2eaeb4e0417e554603
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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