4-Chloro-6,7-dimethoxyquinoline → HCID 22732274, compound

HRID 2084013Notes

Reaction equation

HRID 2084013 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][CH:3]=1.[NH2:16][C:17]1[CH:18]=[C:19]([NH:24][C:25](=[O:35])[C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([N:32]([CH3:34])[CH3:33])[CH:27]=2)[CH:20]=[CH:21][C:22]=1[CH3:23]>C(O)(C)C>[CH3:23][C:22]1[CH:21]=[CH:20][C:19]([NH:24][C:25](=[O:35])[C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([N:32]([CH3:34])[CH3:33])[CH:27]=2)=[CH:18][C:17]=1[NH:16][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 4596104-Chloro-6,7-dimethoxyquinolineHCID 22057981HCID 22057981, compound

Product 1

HCID 22732274HCID 22732274, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
85 °C

Procedure

4-Chloro-6,7-dimethoxyquinoline (WO 98/13350 A1) (150 mg) and N-(3-amino-4-methylphenyl)-3-dimethylaminobenzamide (199 mg) were stirred in isopropanol (5 ml) and heated to 85° C. for 18 hours. After cooling to room temperature the precipitated solid was isolated and washed with isohexane. Filtered solid was impure and so was purified by eluting through a silica column with 10% methanol in methylene chloride. The title compound was obtained as a solid (35 mg); NMR: 2.14 (s, 3H), 2.94 (s, 6H), 3.89 (s, 3H), 3.93 (s, 3H), 6.05 (m, 1H), 6.90 (m, 1H), 7.18 (m, 1H), 7.22 (m, 1H), 7.3 (m, 1H), 7.61 (m, 1H), 7.73 (s, 1H), 7.78 (m, 1H), 8.18 (d, 1H), 8.47 (s, 1H), 10.1 (s, 1H); m/s: M+H+ 457.

Workup

  1. temperatureAfter cooling to room temperature the precipitated solid
  2. customwas isolated
  3. washwashed with isohexane
  4. filtrationFiltered solid
  5. customso was purified
  6. washby eluting through a silica column with 10% methanol in methylene chloride

Sources & evidence

ORD record
ord-c456246741d742ff8c5a6700c00eed75
Source dataset
uspto-grants-2004_04
Patent number
US06716847B2

Reaction notes

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