Dimethylacetamide → HCID 59549438、化合物

HRID 1947774ノート

反応式

HRID 1947774 の反応式
[NH2:1][C:2]1[C:10](Br)=[C:9]2[C:5]([CH2:6][CH2:7][CH:8]2[OH:12])=[CH:4][CH:3]=1.C[C:14]([N:16](C)C)=O>[C-]#N.[Zn+2].[C-]#N.[Zn].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2]>[NH2:1][C:2]1[C:10]([C:14]#[N:16])=[C:9]2[C:5]([CH2:6][CH2:7][CH:8]2[OH:12])=[CH:4][CH:3]=1

参加物

6

反応物 2

HCID 31374DimethylacetamideHCID 685011896-Amino-7-bromoindan-1-ol

生成物 1

HCID 59549438HCID 59549438、化合物

試薬・触媒・溶媒 3

HCID 11186Zinc cyanide (Zn(CN)2)触媒HCID 23994Zinc触媒HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)触媒

反応条件

温度
140 °C

実験手順

A suspension of 6-amino-7-bromoindan-1-ol (1 g, 4.3 mmol), zinc cyanide (290 mg, 2.6 mmol), zinc (140 mg, 2.1 mmol), Pd(dba)3 (10 mol %), and dppf (50 mol %) in dimethylacetamide (8 ml) is heated at 140° C. under nitrogen for six hours. The solvent is distilled off at 100° C. under vacuum, the residue treated with dichloromethane, filtered through Celite, and the filtrate is washed with water. The organic layer is separated, dried over sodium sulfate, filtered, and evaporated. Chromatographic purification by using ethyl acetate/hexane as eluent gives 6-amino-7-cyanoindan-1-ol as solid; LC/MS: 175 (M+1)+.

後処理

  1. distillationThe solvent is distilled off at 100° C. under vacuum
  2. additionthe residue treated with dichloromethane
  3. filtrationfiltered through Celite
  4. washthe filtrate is washed with water
  5. customThe organic layer is separated
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customChromatographic purification

出典と根拠

ORDレコード
ord-d874f7d45d1648088b03b62111abbfe4
出典データセット
uspto-grants-2013_03
特許番号
US08399490B2

反応ノート

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