Hydrochloric Acid → 2-{3-[2-(3,4-Dichlorophenyl)azetidin-1-yl]prop-1-ylamino}-1H-quinolin-4-one

HRID 430075Notes

Reaction equation

HRID 430075 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[CH2:12][CH2:11][N:10]2[CH2:13][CH2:14][CH2:15][NH:16][C:17]2[CH:26]=[C:25]([O:27]C)[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:18]=2)[CH:5]=[CH:6][C:7]=1[Cl:8].Cl>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[CH2:12][CH2:11][N:10]2[CH2:13][CH2:14][CH2:15][NH:16][C:17]2[NH:18][C:19]3[C:24]([C:25](=[O:27])[CH:26]=2)=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 18353676HCID 18353676, compound

Product 1

HCID 183536702-{3-[2-(3,4-Dichlorophenyl)azetidin-1-yl]prop-1-ylamino}-1H-quinolin-4-oneYield 23.3%

Procedure

2-{3-[2-(3,4-Dichlorophenyl)azetidin-1-yl]prop-1-ylamino}-4-methoxyquinoline (0.04 g, 0.096 mmol) was treated at reflux with 10M HCl (4 ml) for 45 min. The reaction mixture was evaporated to dryness, and the residue purified by chromatography on silica gel eluting with 10% (9:1 MeOH/NH3) in dichloromethane to give the title compound as a colourless gum (9 mg, 23%); δH (CD3OD) 1.75 (2H, m), 2.2 (1H, m), 2.45 (1H, m), 2.7-2.9 (2H, m), 3.05 (1H, m), 3.35 (2H, m), 3.55 (1H, m), 5.7 (1H, s), 7.3-7.5 (4H, m), 7.6-7.7 (2H, m), 8.1 (1H, dd); MS (ES+) 402/404 (53/39%, MH+), 230 (60), 187 (100).

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. customthe residue purified by chromatography on silica gel eluting with 10% (9:1 MeOH/NH3) in dichloromethane

Sources & evidence

ORD record
ord-8aa651ee50bd4d3782946a17f219a591
Source dataset
uspto-grants-2001_11
Patent number
US06320051B1

Reaction notes

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