4-Chloro-6,7-dimethoxyquinoline → HCID 22732262, compound

HRID 2084015Notes

Reaction equation

HRID 2084015 reaction equation
[Cl:1][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.[CH3:16][C:17]1[CH:22]=[CH:21][C:20]([NH2:23])=[CH:19][C:18]=1[NH:24][C:25](=[O:36])[C:26]1[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[C:28]([O:34][CH3:35])[CH:27]=1>C(O)(C)C>[ClH:1].[CH3:35][O:34][C:28]1[CH:27]=[C:26]([CH:31]=[CH:30][C:29]=1[O:32][CH3:33])[C:25]([NH:24][C:18]1[CH:19]=[C:20]([CH:21]=[CH:22][C:17]=1[CH3:16])[NH:23][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)=[O:36]

Participants

4

Reactant 2

HCID 4596104-Chloro-6,7-dimethoxyquinolineHCID 16782558HCID 16782558, compound

Product 1

HCID 22732262HCID 22732262, compoundYield 36.2%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
85 °C

Procedure

4-Chloro-6,7-dimethoxyquinoline (315 mg) and N-(2-methyl-5-aminophenyl)-3,4-dimethoxybenzamide (443 mg) were stirred together in isopropanol (10 ml) and heated to 85° C. for 18 hours. After cooling to room temperature the precipitated solid was isolated and washed with isohexane to yield the title compound as a solid (260 mg, 36%); NMR: 2.32 (s, 3H), 3.82 (s, 6H), 3.97 (s, 3H), 3.99 (s, 3H), 6.75 (m, 1H), 7.07 (m, 1H), 7.25 (m, 1H), 7.46 (m, 2H), 7.51 (m, 1H), 7.58 (m, 1H), 7.64 (m, 1H), 8.1 (s, 1H), 8.36 (m, 1H), 9.85 (s, 1H), 10.62 (s, 1H); m/s: M+H+ 474.

Workup

  1. temperatureAfter cooling to room temperature the precipitated solid
  2. customwas isolated
  3. washwashed with isohexane

Sources & evidence

ORD record
ord-b3948544b58e4c55a865a227beff99bb
Source dataset
uspto-grants-2004_04
Patent number
US06716847B2

Reaction notes

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