Hydrochloric Acid → HCID 22732249, compound

HRID 1357705Notes

Reaction equation

HRID 1357705 reaction equation
Cl.[Cl:2][C:3]1[C:12]2[C:7](=[CH:8][C:9]([O:15][CH3:16])=[C:10]([O:13][CH3:14])[CH:11]=2)[N:6]=[CH:5][CH:4]=1.[NH2:17][C:18]1[CH:19]=[C:20]([NH:25][C:26](=[O:37])[C:27]2[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[C:29]([O:35][CH3:36])[CH:28]=2)[CH:21]=[CH:22][C:23]=1[CH3:24]>C(O)(C)C>[ClH:2].[CH3:24][C:23]1[CH:22]=[CH:21][C:20]([NH:25][C:26](=[O:37])[C:27]2[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[C:29]([O:35][CH3:36])[CH:28]=2)=[CH:19][C:18]=1[NH:17][C:3]1[C:12]2[C:7](=[CH:8][C:9]([O:15][CH3:16])=[C:10]([O:13][CH3:14])[CH:11]=2)[N:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4596104-Chloro-6,7-dimethoxyquinolineHCID 22732292N-(3-Amino-4-methylphenyl)-3,4-dimethoxybenzamide

Product 1

HCID 22732249HCID 22732249, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
85 °C

Procedure

Hydrochloric acid (0.15 ml) was added to a mixture of 4-chloro-6,7-dimethoxy quinoline (335 mg) and N-(3-amino-4-methylphenyl)-3,4-dimethoxybenzamide (472 mg) in isopropanol (8 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 (180 mg, 24%); NMR: 2.31 (s, 3H), 3.82 (s, 6H), 3.97 (s, 3H), 3.99 (s, 3H), 6.75 (m, 1H), 7.06 (m, 1H), 7.25 (m, 1H), 7.42 (m, 2H), 7.51 (m, 1H), 7.55 (m, 1H), 7.64 (m, 1H), 8.1 (s, 1H), 8.36 (m, 1H), 9.84 (s, 1H), 10.61 (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-a9249b151dd34fc6bb1debefae4a5259
Source dataset
uspto-grants-2003_07
Patent number
US06593333B1

Reaction notes

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