Hydrochloric Acid → 2-[3-(3,4-Dichlorobenzylamino)prop-1-ylamino]-5-chloro-1H-quinolin-4-one dihydrochloride

HRID 430092Notes

Reaction equation

HRID 430092 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]=[CH:16][C:17]=2[Cl:23])[N:12]=1.[ClH:28]>O1CCOCC1>[ClH:1].[ClH:28].[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)=[C:17]([Cl:23])[CH:16]=[CH:15][CH:14]=2

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 183537112-[3-(3,4-Dichlorobenzylamino)prop-1-ylamino]-5-chloro-4-methoxyquinoline

Product 1

HCID 183536732-[3-(3,4-Dichlorobenzylamino)prop-1-ylamino]-5-chloro-1H-quinolin-4-one dihydrochlorideYield 34%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2-[3-(3,4-Dichlorobenzylamino)prop-1-ylamino]-5-chloro-4-methoxyquinoline (78 mg, 0.18 mmol) in dioxane:concentrated aq. HCl 1:2 (7 ml) was heated at 80° C. for 18 h. Volatiles were evaporated in vacuo and the residue was triturated with CHCl3:tBuOMe 2:1 and filtered to give the title compound as a colourless solid, (30 mg, 34%). δH (CD3OD) 2.10-2.27 (m, 2H, CH2CH2CH2), ca. 3.27 (t, merged with MeOH peak, 2H, CH2CH2CH2), 3.67 (t, J=6.7, 2H, CH2CH2CH2), 4.29 (s, 2H, Ar—CH2—N), 6.39 (s, 1H, HCC═O), 7.47-7.56 (m, 2H, Ar—H), 7.60-7.72 (m, 2H, Ar—H), 7.78-7.90 (m, 2H, Ar—H); MS (ES+) 410 (MH+, 59%), 235 (100).

Workup

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

Sources & evidence

ORD record
ord-cd91ce9a23004f5c92bb6166e7ad1401
Source dataset
uspto-grants-2001_11
Patent number
US06320051B1

Reaction notes

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