2-[3-(3,4-Dichlorobenzylamino)prop-1-ylamino]-4-methoxy-6-methylquinoline → 2-[3-(3,4-Dichlorobenzylamino)prop-1-ylamino]-6-methyl-1H-quinolin-4-one dihydrochloride

HRID 430089Notes

Reaction equation

HRID 430089 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:24]=[CH:25][C:26]=1[Cl:27])[CH2:5][NH:6][CH2:7][CH2:8][CH2:9][NH:10][C:11]1[CH:20]=[C:19]([O:21]C)[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([CH3:23])[CH:17]=2)[N:12]=1>O1CCOCC1.Cl>[ClH:1].[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([CH:24]=[CH:25][C:26]=1[Cl:27])[CH2:5][NH:6][CH2:7][CH2:8][CH2:9][NH:10][C:11]1[NH:12][C:13]2[C:18]([C:19](=[O:21])[CH:20]=1)=[CH:17][C:16]([CH3:23])=[CH:15][CH:14]=2

Participants

4

Reactant 1

HCID 183537582-[3-(3,4-Dichlorobenzylamino)prop-1-ylamino]-4-methoxy-6-methylquinoline

Product 1

HCID 183537372-[3-(3,4-Dichlorobenzylamino)prop-1-ylamino]-6-methyl-1H-quinolin-4-one dihydrochlorideYield 237.5%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

2-[3-(3,4-Dichlorobenzylamino)prop-1-ylamino]-4-methoxy-6-methylquinoline (50 mg, 0.12 mmol) in 2 ml dioxane and 5 ml concentrated aq. HCl was heated at 100° C. for 18 h. Volatiles were evaporated in vacuo and the residue was triturated with CHCl3 and filtered to give the title compound as a yellow powder, (44 mg, 76%). δH (CD3OD, 400 MHz) 1.97-2.08 (m, 2H, CH2CH2CH2), 2.35 (s, 3H, Ar—CH3), 3.12 (t, J=7.8, 2H, CH2CH2CH2), 3.53 (t, J=6.7, 2H, CH2CH2CH3), 4.13 (s, 2H, ArCH2N), 6.20 (s, 1H, HCC═O), 7.36 (dd, J 8.2, 2.0, 1H, Ar—H), 7.47-7.52 (m, 2H, Ar—H), 7.57-7.66 (m, 2H, Ar—H), 7.76 (s, 1H, Ar—H); MS (ES+) 390 (MH+, 64%), 215 (100).

Workup

  1. customVolatiles were evaporated in vacuo
  2. customthe residue was triturated with CHCl3
  3. filtrationfiltered

Sources & evidence

ORD record
ord-937ab7f2f48846a196c882f1b62f0956
Source dataset
uspto-grants-2001_11
Patent number
US06320051B1

Reaction notes

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