Ammonium Chloride → 2-(1-Naphthalenyl)-6,7-methylenedioxyquinolin-4-one

HRID 38649Notes

Reaction equation

HRID 38649 reaction equation
[C:1]([C:4]1[C:5]([NH:13][C:14]([C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:19]=[CH:18][CH:17]=2)=O)=[CH:6][C:7]2[O:11][CH2:10][O:9][C:8]=2[CH:12]=1)(=[O:3])[CH3:2].CC(C)([O-])C.[K+].[Cl-].[NH4+]>C(O)(C)(C)C>[C:16]1([C:14]2[CH2:2][C:1](=[O:3])[C:4]3[C:5](=[CH:6][C:7]4[O:11][CH2:10][O:9][C:8]=4[CH:12]=3)[N:13]=2)[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 926571N-(6-acetyl-1,3-benzodioxol-5-yl)naphthalene-1-carboxamideHCID 23665647Potassium tert-butoxide

Product 1

HCID 666589682-(1-Naphthalenyl)-6,7-methylenedioxyquinolin-4-oneYield 52%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

Into a suspension of 150 (2.95 mmol) in t-butyl alcohol (100 mL) was added potassium t-butoxide (1.66 g, 14.7 mmol). The mixture was refluxed under argon for 12 h, cooled, and poured into a 10% ammonium chloride solution (100 mL). The solid precipitate was collected and washed with EtOH. The crude product was purified by flash chromatography (silica gel, CH2Cl2:EtOH 16:1-10:1). Yield 52% from 150 as a grayish-white solid; mp>350° C.; ESI-MS (Positive mode): m/z 316 [M+H]+; 1H-NMR (DMSO-d6, 8): 6.08 (1H, s), 6.15 (2H, s), 7.03 (1H, s), 7.46 (1H, s), 7.56-7.63 (2H, m), 7.63-7.70 (2H, m), 7.83 (1H, d, J=7.6 Hz), 8.06 (1H, d, J=7.6 Hz), 8.11 (1H, d, J=7.6 Hz), 11.90 (1H, s). IR (KBr): 1653 (C═O) cm−1; Anal. Calcd for C20H13NO3: C, 76.18; H, 4.16; N, 4.44. Found: C, 75.60; H, 3.94; N, 4.29.

Workup

  1. temperatureThe mixture was refluxed under argon for 12 h
  2. temperaturecooled
  3. customThe solid precipitate was collected
  4. washwashed with EtOH
  5. customThe crude product was purified by flash chromatography (silica gel, CH2Cl2:EtOH 16:1-10:1)

Sources & evidence

ORD record
ord-77b6f1a7ecae4f7390b18f32f42f41c7
Source dataset
uspto-grants-2013_09
Patent number
US08524740B2

Reaction notes

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