Ammonium formate → 2-(4-(4-Chloro-3-(trifluoromethyl)phenoxy)phenyl)ethanamine

HRID 920292ノート

反応式

HRID 920292 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][N+:17]([O-])=O)=[CH:11][CH:10]=2)=[CH:4][C:3]=1[C:20]([F:23])([F:22])[F:21].C([O-])=O.[NH4+]>CO.O.[Zn]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][NH2:17])=[CH:11][CH:10]=2)=[CH:4][C:3]=1[C:20]([F:21])([F:22])[F:23]

参加物

6

反応物 2

HCID 2723923Ammonium formateHCID 67775633Chloro-4-(4-(2-nitroethyl)phenoxy)-2-(trifluoromethyl)benzene

生成物 1

HCID 677755482-(4-(4-Chloro-3-(trifluoromethyl)phenoxy)phenyl)ethanamine収率 36.5%

試薬・触媒・溶媒 3

HCID 23994Zinc触媒HCID 887Methanol溶媒HCID 962Water溶媒

反応条件

温度
80 °C

実験手順

To a solution of 1-chloro-4-(4-(2-nitroethyl)phenoxy)-2-(trifluoromethyl)benzene (21 g, 60.7 mmol) and ammonium formate (30.6 g, 486 mmol) in methanol (250 mL) and water (250 mL), was added zinc powder (15.89 g, 243 mmol). The reaction mixture was stirred at 80° C. for 2 h, filtered through a glass grit and washed with methanol. The filtrate was concentrated and the residue was extracted with DCM (200 mL), and then washed with sat. NaHCO3 (100 mL), brine, and dried over anhydrous Na2SO4 and concentrated. Purification via FC (DCM/CH3OH=100/8) afforded the title compound (7.0 g) as a yellow oil.

後処理

  1. filtrationfiltered through a glass grit
  2. washwashed with methanol
  3. concentrationThe filtrate was concentrated
  4. extractionthe residue was extracted with DCM (200 mL)
  5. washwashed with sat. NaHCO3 (100 mL), brine
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated
  8. customPurification via FC (DCM/CH3OH=100/8)

出典と根拠

ORDレコード
ord-66714892334d4d1e838afa23e3f840d3
出典データセット
uspto-grants-2016_03
特許番号
US09273054B2

反応ノート

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