4-Chloro-6,7-dimethoxyquinoline → HCID 22132789, compound

HRID 1857203Notes

Reaction equation

HRID 1857203 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]([C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=2)=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].Cl[C:20]1[C:29]2[C:24](=[CH:25][C:26]([O:32][CH3:33])=[C:27]([O:30][CH3:31])[CH:28]=2)[N:23]=[CH:22][CH:21]=1>CN(C)C1C=CN=CC=1.C1(C)C(C)=CC=CC=1>[CH3:31][O:30][C:27]1[CH:28]=[C:29]2[C:24](=[CH:25][C:26]=1[O:32][CH3:33])[N:23]=[CH:22][CH:21]=[C:20]2[O:18][C:15]1[CH:16]=[CH:17][C:12]([C:10]([C:7]2[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)=[O:11])=[CH:13][CH:14]=1

Participants

5

Reactant 2

HCID 4596104-Chloro-6,7-dimethoxyquinolineHCID 110968174-Hydroxy-4'-nitrobenzophenone

Product 1

HCID 22132789HCID 22132789, compoundYield 36.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 7237O-XyleneSolvent

Procedure

Under argon, 4-hydroxyphenyl 4-nitrophenyl ketone (370 mg) obtained in Example 134 and 4-dimethylaminopyridine (204 mg) were added to xylene (5 ml), and the admixture was stirred at room temperature for 1 hour. 4-Chloro-6,7-dimethoxyquinoline (340 mg) was added, and the mixture was then refluxed with heat for 23 hours. The reaction mixture was treated in the same manner as described in Example 130 to obtain 238 mg of the title compound (yield: 36%).

Workup

  1. temperaturethe mixture was then refluxed
  2. temperaturewith heat for 23 hours
  3. additionThe reaction mixture was treated in the same manner

Sources & evidence

ORD record
ord-c79f63746fb14822b4e0de777521086e
Source dataset
uspto-grants-2000_11
Patent number
US06143764

Reaction notes

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