4-Chloro-6,7-dimethoxyquinoline → HCID 22132757, compound

HRID 1857205Notes

Reaction equation

HRID 1857205 reaction equation
[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([C:10]([C:12]3[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=3)=[O:11])=[CH:4][C:3]=2[O:2]1.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:5]2[CH:6]=[CH:7][C:8]3[O:9][CH2:1][O:2][C:3]=3[CH:4]=2)=[O:11])=[CH:13][CH:14]=1

Participants

5

Reactant 2

HCID 4596104-Chloro-6,7-dimethoxyquinolineHCID 22132652HCID 22132652, compound

Product 1

HCID 22132757HCID 22132757, compoundYield 38%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 7237O-XyleneSolvent

Procedure

Under argon, 4-hydroxyphenyl 3, 4-methylenedioxyphenyl ketone (202 mg) obtained in Example 136 and 4-dimethylaminopyridine (112 mg) were added to xylene (2 ml), and the admixture was stirred at room temperature for 1 hour. 4-Chloro-6,7-dimethoxyquinoline (187 mg) was added, and the admixture was refluxed with heat for 20 hours. The reaction mixture was treated in the same manner as described in Example 124 to obtain 135 mg of the title compound (yield: 38%).

Workup

  1. temperaturethe admixture was refluxed
  2. temperaturewith heat for 20 hours
  3. additionThe reaction mixture was treated in the same manner

Sources & evidence

ORD record
ord-f1670210fbc341d8b272f9b5c173ce02
Source dataset
uspto-grants-2000_11
Patent number
US06143764

Reaction notes

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