Methanol → HCID 20636410, compound

HRID 49223Notes

Reaction equation

HRID 49223 reaction equation
COC1C=C(C=C[N:11]2[CH:20]=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]2=[O:21])C=CN=1.[CH3:22][OH:23]>[Pd]>[CH3:22][O:23][C:12]1[CH:13]=[C:18]([CH2:17][CH2:16][C:19]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12](=[O:21])[NH:11][CH:20]=2)[CH:19]=[CH:20][N:11]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 86589052HCID 86589052, compound

Product 1

HCID 20636410HCID 20636410, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

1.1 g of the above (E/Z) mixture of 4-[2-(2-methoxy-pyridin-4-yl)-vinyl-2H-isoquinolin-1-one in 20 ml of methanol are hydrogenated in the presence of 0.6 g of Pd/C (10%). Filtration through Celite, washing with a lot of methanol, concentrating by evaporation and column chromatography (SiO2, methylene chloride/acetone 3:1→acetone) yield 4-[2-(2-methoxy-pyridin-4-yl)-ethyl]-2H-isoquinolin-1-one; 1H NMR (DMSO-d6) δ11.10 (sb, HN), 8.22 (d, 1H), 8.03 (d, 1H), 7.81 (d, 1H), 7.75 (t, 1H), 7.50 (t, 1H), 6.92 (m, 1H), 6.88 (d, 1H), 6.70 (s, 1H), 3.80 (s, H3C), 2.93 (m, 2H), 2.84 (m, 2H).

Workup

  1. filtrationFiltration through Celite
  2. washwashing with a lot of methanol
  3. concentrationconcentrating by evaporation and column chromatography (SiO2, methylene chloride/acetone 3:1→acetone)

Sources & evidence

ORD record
ord-a7fb00ca255341ac9f543ab64e795a8c
Source dataset
uspto-grants-2004_03
Patent number
US06706731B2

Reaction notes

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