Sodium Hydroxide → 2-(2-Benzyloxyphenyl)-6-morpholinoquinolin-4-one

HRID 38642Notes

Reaction equation

HRID 38642 reaction equation
[C:1]([C:4]1[CH:9]=[C:8]([N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)[CH:7]=[CH:6][C:5]=1[NH:16][C:17](=O)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)(=[O:3])[CH3:2].[OH-].[Na+]>O1CCOCC1>[CH2:25]([O:24][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[C:17]1[CH2:2][C:1](=[O:3])[C:4]2[C:5](=[CH:6][CH:7]=[C:8]([N:10]3[CH2:15][CH2:14][O:13][CH2:12][CH2:11]3)[CH:9]=2)[N:16]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66659421N-(2-Acetyl-4-morpholinophenyl)-2-benzyloxybenzamide

Product 1

HCID 666596922-(2-Benzyloxyphenyl)-6-morpholinoquinolin-4-oneYield 118.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 92 (1.2 g, 2.7 mmol) in 1,4 dioxane (150 ml) was added NaOH (0.9 g, 21.4 mmol). The mixture was refluxed for 5 h, concentrated and added 10% NH4Cl (100 ml). The precipitate was collected and washed with H2O and acetone. The crude product was purified by column chromatography (silica gel, CHCl3:MeOH=25:1) to give 113 as yellow solid (1.3 g, 3.2 mmol). Yield: 65.4%; mp 281-283° C.; MS (EI, 70 eV): m/z 412.4 (M+); 1H-NMR (DMSO-d6. 200 MHz): δ 3.15 (m, 4H), 3.77 (m, 4H), 5.12 (s, 2H), 6.30 (s, 1H), 7.36-7.50 (m, 11H), 7.66 (d, J=9.2 Hz, 1H), 11.57 (s, 1H); Anal. Calcd for C26H24N2O3; C, 75.71; H, 5.86; N, 6.79.

Workup

  1. temperatureThe mixture was refluxed for 5 h
  2. concentrationconcentrated
  3. additionadded 10% NH4Cl (100 ml)
  4. customThe precipitate was collected
  5. washwashed with H2O and acetone
  6. customThe crude product was purified by column chromatography (silica gel, CHCl3:MeOH=25:1)

Sources & evidence

ORD record
ord-5e2a2dfcd301416784dacd3fbed8327a
Source dataset
uspto-grants-2013_09
Patent number
US08524740B2

Reaction notes

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