2,6-Dihydroxy-4-methylquinoline → 4-Methyl-6-{3-[4-(4-fluorobenzyl)-piperazin-1-yl]-propoxy}-2-oxo-1,2-dihydroquinoline

HRID 224770Notes

Reaction equation

HRID 224770 reaction equation
[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([OH:12])[CH:10]=2)[NH:5][C:4](=[O:13])[CH:3]=1.[F:14][C:15]1[CH:31]=[CH:30][C:18]([CH2:19][N:20]2[CH2:25][CH2:24][N:23]([CH2:26][CH2:27][CH2:28]Cl)[CH2:22][CH2:21]2)=[CH:17][CH:16]=1>>[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH2:28][CH2:27][CH2:26][N:23]3[CH2:24][CH2:25][N:20]([CH2:19][C:18]4[CH:17]=[CH:16][C:15]([F:14])=[CH:31][CH:30]=4)[CH2:21][CH2:22]3)[CH:10]=2)[NH:5][C:4](=[O:13])[CH:3]=1

Participants

3

Reactant 2

HCID 6002882,6-Dihydroxy-4-methylquinolineHCID 201531693-[4-(4-Fluorobenzyl)-piperazin-1-yl]-propyl chloride

Product 1

HCID 233304344-Methyl-6-{3-[4-(4-fluorobenzyl)-piperazin-1-yl]-propoxy}-2-oxo-1,2-dihydroquinoline

Procedure

In a manner analogous to that described in Example 5, by the appropriate reaction of 4-methyl-6-hydroxy-2-oxo-1,2-dihydroquinoline with 3-[4-(4-fluorobenzyl)-piperazin-1-yl]-propyl chloride, there is obtained 4-methyl-6-{3-[4-(4-fluorobenzyl)-piperazin-1-yl]-propoxy}-2-oxo-1,2-dihydroquinoline which, after recrystallization from ethanol, melts at 178°-180° C.

Sources & evidence

ORD record
ord-4b590de798744c65b868757996b371ef
Source dataset
uspto-grants-1980_11
Patent number
US04234585

Reaction notes

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