Water → 4-[(Pyridin-4-yl)methyl]isoquinolin-1(2H)-one

HRID 396216Notes

Reaction equation

HRID 396216 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]([C:18]#[N:19])=[CH:11][C:12]1[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=1.O>[Ni].C1COCC1>[N:15]1[CH:16]=[CH:17][C:12]([CH2:11][C:10]2[C:5]3[C:4](=[CH:9][CH:8]=[CH:7][CH:6]=3)[C:3](=[O:2])[NH:19][CH:18]=2)=[CH:13][CH:14]=1

Participants

5

Reactant 2

HCID 962WaterHCID 72801199HCID 72801199, compound

Product 1

HCID 230036234-[(Pyridin-4-yl)methyl]isoquinolin-1(2H)-one

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

In the presence of 5×40 g of Raney nickel (added at intervals), 163 g (617 mmol) of 2-[(1-cyano-2-(pyridin-4-yl)-vinyl]-benzoic acid methyl ester are hydrogenated in 3 liters of THF at 40° C. for 90 hours. The reaction mixture is filtered, and the filtrate is concentrated by evaporation and crystallised from acetonitrile/ethyl acetate (→title compound). Further product can be obtained from the mother liquor by chromatography (SiO2; ethyl acetate→acetone): m.p. 189-190° C.; FAB-MS: (M+H)+=237; 1H NMR (DMSO-d6) 11.27 (sb, HN), 8.45 (d, 2H), 8.23 (d, 1H), 7.65 (t, 1H), 7.48 (m, 2H), 7.27 (d, 2H), 7.18 (s, 1H), 4.05 (s, 2H); Anal. calc. (Cl5H12N2O.0.05 H2O) C 75.96%, H 5.14%, N 11.81%; found C 75.8%, H 5.2%, N 11.9%.

Workup

  1. filtrationThe reaction mixture is filtered
  2. concentrationthe filtrate is concentrated by evaporation
  3. customcrystallised from acetonitrile/ethyl acetate (→title compound)
  4. customFurther product can be obtained from the mother liquor by chromatography (SiO2; ethyl acetate→acetone)

Sources & evidence

ORD record
ord-33cecbc9953b4e26990f9fcdf07e13e4
Source dataset
uspto-grants-2003_08
Patent number
US06608071B2

Reaction notes

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