2,5-Dichloro-4-methoxyquinoline → 2-[3-(3,4-Dichlorobenzylamino)prop-1-ylamino]-5-chloro-4-methoxyquinoline

HRID 430091Notes

Reaction equation

HRID 430091 reaction equation
Cl[C:2]1[CH:11]=[C:10]([O:12][CH3:13])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[Cl:14])[N:3]=1.[NH2:15][CH2:16][CH2:17][CH2:18][NH:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[C:23]([Cl:28])[CH:22]=1.CO.N.C(Cl)Cl>>[Cl:28][C:23]1[CH:22]=[C:21]([CH:26]=[CH:25][C:24]=1[Cl:27])[CH2:20][NH:19][CH2:18][CH2:17][CH2:16][NH:15][C:2]1[CH:11]=[C:10]([O:12][CH3:13])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[Cl:14])[N:3]=1

Participants

4

Reactant 3

HCID 183537032,5-Dichloro-4-methoxyquinolineHCID 18353717N-(3-aminoprop-1-yl)-3,4-dichlorobenzylamineHCID 21584172Ammonia methanol dichloromethane

Product 1

HCID 183537112-[3-(3,4-Dichlorobenzylamino)prop-1-ylamino]-5-chloro-4-methoxyquinoline

Conditions

Temperature
100 °C

Procedure

A mixture of 2,5-dichloro-4-methoxyquinoline (0.12 g, 0.53 mmol) and N-(3-aminoprop-1-yl)-3,4-dichlorobenzylamine (0.37 g) was heated at 100° C. for 8 h. The resulting mixture was submitted to column chromatography (silica gel, MeOH:NH3:CH2Cl2 10:1:150→10:1:100) to give the title compound as a colourless film, (93 mg, 41%). δH (CDCl3) 1.70-1.87 (m, 3H+H2O), 2.74 (t, J=6.3, 2H), 3.54-3.65 (m, 2H), 3.72 (s, 2H), 3.91 (s, 3H), 5.22 (br, t, 1H), 5.90 (s, 1H), 7.10-7.17 (m, 2H), 7.28-7.37 (m, 2H), 7.40-7.45 (m, 2H); MS (ES+) 424 (MH+, 37%), 249 (100).

Sources & evidence

ORD record
ord-04f3868316af49e28e84e89405f5af1c
Source dataset
uspto-grants-2001_11
Patent number
US06320051B1

Reaction notes

Loading…