N-(3-aminoprop-1-yl)-3,4-dichlorobenzylamine → 2-[3-(3,4-Dichlorobenzylamino)prop-1-ylamino]-4-methoxy-6-methylquinoline
Reaction equation
Cl[C:2]1[CH:11]=[C:10]([O:12][CH3:13])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH3:14])[CH:8]=2)[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]=[C:7]([CH3:14])[CH:8]=2)[N:3]=1Participants
4
Conditions
- Temperature
- 100 °C
Procedure
A mixture of 2-chloro-4-methoxy-6-methylquinoline (94 mg, 0.45 mmol) and N-(3-aminoprop-1-yl)-3,4-dichlorobenzylamine (0.21 g) was heated at 70° C. for 15 h, at 100° C. for 2 h, and then at 120° C. for 15 h. The resulting mixture was submitted to column chromatography (silica gel, MeOH:NH3:CH2Cl2 20:2:100) to give the title compound as a red film, (65 mg, 36%). δH (CDCl3) 1.72-1.89 (m, 3H+H2O), 2.42 (s, 3H), 2.74 (t, J=6.4, 2H), 3.53-3.65 (m, 2H), 3.71 (s, 2H), 3.94 (s, 3H), 5.06 (br, s, 1H), 5.87 (s, 1H), 7.12 (dd, J=8.2. 2.0, 1H), 7.28-7.36 (m, 2H), 7.40-7.48 (m, 2H), 7.72 (br, s, 1H): MS (ES+) 404 (MH+, 43%), 229 (100).
Sources & evidence
- ORD record
- ord-16a4ba777fd741df94d6a68f8b016da1
- Source dataset
- uspto-grants-2001_11
- Patent number
- US06320051B1
Reaction notes
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