Dimethylacetamide → HCID 59549438, 화합물

HRID 1947774노트

반응식

HRID 1947774 반응식
[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

참가 물질

6

반응물 2

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

생성물 1

HCID 59549438HCID 59549438, 화합물

시약·촉매·용매 3

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

반응 조건

온도
140 °C

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-d874f7d45d1648088b03b62111abbfe4
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08399490B2

반응 노트

불러오는 중…