2-(2-Benzyloxyphenyl)-6-morpholinoquinolin-4-one → HCID 136407516, compound

HRID 38643Notes

Reaction equation

HRID 38643 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[CH2:24][C:23](=[O:25])[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([N:26]3[CH2:31][CH2:30][O:29][CH2:28][CH2:27]3)[CH:21]=2)[N:16]=1)C1C=CC=CC=1>CO.[Pd]>[OH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[CH2:24][C:23](=[O:25])[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([N:26]3[CH2:31][CH2:30][O:29][CH2:28][CH2:27]3)[CH:21]=2)[N:16]=1

Participants

4

Reactant 1

HCID 666596922-(2-Benzyloxyphenyl)-6-morpholinoquinolin-4-one

Product 1

HCID 136407516HCID 136407516, compoundYield 81.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a suspension of 113 (0.4 g, 1.0 mmol) in MeOH (400 ml) was hydrogenated in the presence of 10% Pd/C (0.1 g) at 25□ for 3 h. The catalyst was filtered off and the filtrate was evaporated. The crude product was purified by column chromatography (SiO2, CHCl3:MeOH=25:1) to give 134 as yellow solid. (0.3 g, 0.9 mmol). Yield: 81.5%; mp 290-291° C.; MS (EI, 70 eV): m/z 322.2 (M+); IR (KBr): 1612.56 (C═O), 2969.54 (—NH) cm−1; 1H-NMR (MeOD-d4, 400 MHz) δ 3.30 (m, 4H), 3.87 (m, 4H), 4.48 (s, 1H), 6.64 (s, 1H), 7.02 (d, J=8.8 Hz, 1H), 7.04 (d, J=8.8 Hz, 1H); 7.40 (t, J=8.0 Hz, 1H), 7.60 (d, J=8.8 Hz, 2H), 7.65 (d, J=2.0 Hz, 1H), 7.72 (d, J=9.2 Hz, 1H); Anal. Calcd for C19H18N2O3; C, 70.79; H, 5.63; N, 8.69.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate was evaporated
  3. customThe crude product was purified by column chromatography (SiO2, CHCl3:MeOH=25:1)

Sources & evidence

ORD record
ord-7aa4cee06bd7449eb6345061ae7d0552
Source dataset
uspto-grants-2013_09
Patent number
US08524740B2

Reaction notes

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