Ammonium Chloride → 5-Amino-1-chloroisoquinoline

HRID 908311

反応式

HRID 908311 の反応式
[CH:1]1[C:10]2[C:5](=[C:6](C3C=C4C(=CC=3)C=C(NC(C3SC=CC=3)=O)C=C4)[CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1.[NH4+:29].[Cl-:30]>[Fe].CCO.O>[Cl:30][C:1]1[C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([NH2:29])[C:5]=2[CH:4]=[CH:3][N:2]=1

参加物

5

反応物 2

HCID 25517Ammonium ChlorideHCID 11990812N-[6-(Isoquinolin-5-yl)naphthalen-2-yl]thiophene-2-carboxamide

生成物 1

HCID 4597715-Amino-1-chloroisoquinoline収率 175.4%

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 19096565Water ethanol溶媒

反応条件

温度
80 °C

実験手順

To a 1000 mL 3-neck round-bottomed flask containing 1-chloro-5-nitroisoquinoline (Step 1, 8.200 g, 39.3 mmol) was added Iron powder (11.80 g, 211.2 mmol), while under a flow of inert gas. A 3:1 mixture of EtOH/H2O (240 mL), and NH4Cl (1.19 g, 22.4 mmol) were added. The mixture was heated to 80° C., while stirring under inert atmosphere for 1 hour. The oil bath was removed and the mixture was allowed to cool to ambient temperature. The crude material was filtered through a plug of Celite, and the filtrate was concentrated in-vacuo. Recrystallization from DCM/Hexanes, and further washing the solid with hexanes (3×100 mL) afforded a brown crystalline solid, which was titled product (7.015 g, 39.3 mmol). MS (ESI pos. ion) m/z: 179 (M+H). Calc'd Exact Mass for C9H7N2Cl: 178.5

後処理

  1. additionwere added
  2. customThe oil bath was removed
  3. temperatureto cool to ambient temperature
  4. filtrationThe crude material was filtered through a plug of Celite
  5. concentrationthe filtrate was concentrated in-vacuo
  6. customRecrystallization from DCM/Hexanes
  7. washfurther washing the solid with hexanes (3×100 mL)
  8. customafforded a brown crystalline solid, which

出典と根拠

ORDレコード
ord-5efaa73899c048bdadd693b8c1e554c6
出典データセット
uspto-grants-2011_09
特許番号
US08017601B2

関連ノート

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