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

HRID 396215ノート

反応式

HRID 396215 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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%.

後処理

  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

出典と根拠

ORDレコード
ord-cc57883b468047929c7df98e91416119
出典データセット
uspto-grants-2003_08
特許番号
US06608071B2

反応ノート

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