Methyl iodide → HCID 20133480, compound

HRID 845029Notes

Reaction equation

HRID 845029 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([F:18])[C:11]=1[N:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1)[N:8]([C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=1)[CH:7]=[C:6]([C:26]([OH:28])=[O:27])[C:5]2=[O:29].[CH3:30]I>CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([F:18])[C:11]=1[N:12]1[CH2:17][CH2:16][N:15]([CH3:30])[CH2:14][CH2:13]1)[N:8]([C:19]1[CH:20]=[CH:21][C:22]([OH:25])=[CH:23][CH:24]=1)[CH:7]=[C:6]([C:26]([OH:28])=[O:27])[C:5]2=[O:29]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 21290575HCID 21290575, compound

Product 1

HCID 20133480HCID 20133480, compoundYield 39.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 6,8-Difluoro-1-(4-hydroxyphenyl)-7-(1-piperazinyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (4.18 g) in DMF (29 ml) is added a solution of methyl iodide (7.7 g) in DMF (20 ml). The mixture is heated in a stainless steel autoclave on an oil bath at 110°-120° C. for 5 hours. DMF is distilled off under reduced pressure, and to the residue is added 10% aqueous sodium hydroxide to regulate pH 13. The insoluble substance is filtered off, and the remaining mixture is regulated to pH 8 with acetic acid. The precipitated crystals are separated by filtration, washed with water, dried, and then recrystallized from DMF to give 6,8-difluoro-1-(4-hydroxyphenyl)-7-(4-methyl-1-piperazinyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (1.7 g) as pale yellowish white crystals, m.p. >300° C.

Workup

  1. distillationDMF is distilled off under reduced pressure
  2. additionto the residue is added 10% aqueous sodium hydroxide
  3. filtrationThe insoluble substance is filtered off
  4. customThe precipitated crystals are separated by filtration
  5. washwashed with water
  6. customdried
  7. customrecrystallized from DMF

Sources & evidence

ORD record
ord-ba9b987122254ca5a2cf2ea2a60442ef
Source dataset
uspto-grants-1988_07
Patent number
US04755513

Reaction notes

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