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

HRID 396215Notes

Reaction equation

HRID 396215 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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%.

Workup

  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

Sources & evidence

ORD record
ord-cc57883b468047929c7df98e91416119
Source dataset
uspto-grants-2003_08
Patent number
US06608071B2

Reaction notes

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