4,7-Dichloroquinoline → HCID 67248748, compound

HRID 1190887Notes

Reaction equation

HRID 1190887 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:12]([O:14][CH3:15])=[O:13])[CH:5]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:7]=1.Cl[C:17]1[C:26]2[C:21](=[CH:22][C:23]([Cl:27])=[CH:24][CH:25]=2)[N:20]=[CH:19][CH:18]=1>C(O)C>[Cl:27][C:23]1[CH:22]=[C:21]2[C:26]([C:17]([NH:1][C:2]3[CH:3]=[C:4]([C:12]([O:14][CH3:15])=[O:13])[CH:5]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:7]=3)=[CH:18][CH:19]=[N:20]2)=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 68664,7-DichloroquinolineHCID 66831Dimethyl 5-aminoisophthalate

Product 1

HCID 67248748HCID 67248748, compoundYield 78.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1,3-dimethyl 5-aminobenzene-1,3-dicarboxylate (2.09 g, 10 mmol) and 4,7-dichloroquinoline (1.98 g, 1 eq) were refluxed in 200 mL of ethanol for 3 h. The reaction mixture was then cooled to room temperature and the precipitate was removed by filtration and washed successively with a saturated aqueous solution of NaHCO3, water, ethanol and then petroleum ether to yield expected compound as a yellow powder (2.90 g, 78% yield). m/z (ESI) 371.0 [M+H]+.

Workup

  1. customthe precipitate was removed by filtration
  2. washwashed successively with a saturated aqueous solution of NaHCO3, water, ethanol

Sources & evidence

ORD record
ord-92ad79f2fe8a4cd1ac57133108030a97
Source dataset
uspto-grants-2014_03
Patent number
US08680095B2

Reaction notes

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