Dimethylformamide dimethyl acetal → 1-(3,5-Dimethylanilino)-4-[(pyridin-4-yl)-methyl]-isoquinoline

HRID 396215노트

반응식

HRID 396215 반응식
[C:1]([C:3]([C:11]1[CH:19]=[CH:18][CH:17]=[CH:16][C:12]=1[C:13](O)=O)=[CH:4][C:5]1[CH:10]=[CH:9][N:8]=[CH:7][CH:6]=1)#[N:2].COC(OC)[N:23]([CH3:25])C>C(Cl)Cl>[CH3:11][C:3]1[CH:1]=[C:25]([CH:6]=[C:5]([CH3:10])[CH:4]=1)[NH:23][C:13]1[C:12]2[C:11](=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:3]([CH2:4][C:5]2[CH:10]=[CH:9][N:8]=[CH:7][CH:6]=2)=[CH:1][N:2]=1

참가 물질

4

반응물 2

HCID 78373Dimethylformamide dimethyl acetalHCID 72785147(1-Cyano-2-(pyridin-4-yl)-vinyl]-benzoic acid

생성물 1

HCID 98627391-(3,5-Dimethylanilino)-4-[(pyridin-4-yl)-methyl]-isoquinoline

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

With the exclusion of moisture, 211 g (0.843 mol) of 2-[(1-cyano-2-(pyridin-4-yl)-vinyl]-benzoic acid are suspended in 3.3 liters of CH2Cl2; 169 ml (=90%, 1.1 mol) of dimethylformamide dimethylacetal (Fluka, Buchs, Switzerland) are added at room temperature, and stirring is carried out for 22 hours to complete the reaction. The reaction mixture is filtered, and the residue is washed thoroughly with CH2Cl2 and discarded. Concentration of the filtrate by evaporation, chromatography (SiO2; ethyl acetate) and crystallisation from ethyl acetate/hexane yield the title compound: m.p. 102-104° C.; FAB-MS: (M+H)+=265; 1H NMR (DMSO-d6) 8.76 (d, 2H), 7.97 (d, 1H), 7.76 (m, 3H), 7.65 (m, 2H), 7.60 (s, 1H), 3.86 (s, 3H); Anal. calc. (C16H12N2O2) C 72.72%, H 4.58%, N 10.60%; found C 72.7%, H 4.8%, N 10.5%.

후처리

  1. customthe reaction
  2. filtrationThe reaction mixture is filtered
  3. washthe residue is washed thoroughly with CH2Cl2
  4. customConcentration of the filtrate by evaporation, chromatography (SiO2; ethyl acetate) and crystallisation from ethyl acetate/hexane

출처 및 근거

ORD 기록
ord-cc57883b468047929c7df98e91416119
출처 데이터셋
uspto-grants-2003_08
특허 번호
US06608071B2

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