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

HRID 430075ノート

反応式

HRID 430075 の反応式
[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]

参加物

3

反応物 2

HCID 313Hydrochloric AcidHCID 18353676HCID 18353676、化合物

生成物 1

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

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-8aa651ee50bd4d3782946a17f219a591
出典データセット
uspto-grants-2001_11
特許番号
US06320051B1

反応ノート

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