Dimethylformamide → HCID 20427616, compound

HRID 615332Notes

Reaction equation

HRID 615332 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:20])[C:7]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:8][N:9]2NC=O)=[CH:4][C:3]=1[F:21].[C:22](=[O:25])([O-])[O-].[K+].[K+].CI.[CH3:30][N:31](C)C=O>>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:20])[C:7]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:8][NH:9]2)=[C:4]([NH:31][CH2:30][CH:22]=[O:25])[C:3]=1[F:21]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 3021289[7-Chloro-3-(ethoxycarbonyl)-6-fluoro-4-oxoquinolin-1(4H)-yl]methanimidic acid

Product 1

HCID 20427616HCID 20427616, compound

Conditions

Temperature
25 °C

Procedure

A mixture of 14.65 g (0.047 mole) of ethyl 7-chloro-6-fluoro-1-(formylamino)-1,4-dihydro-4-oxo-3-quinolinecarboxylate (Preparation 2), 12.9 g (0.094 mole) of potassium carbonate and 200 ml of dimethylformamide was stirred at 25° C. for 90 minutes. Methyl iodide (20.0 g, 0.141 mole) was then added and the reaction mixture was stirred at room temperature for 90 minutes. The dimethylformamide was removed in high vacuum at 50° C., and the residue was partitioned between 250 ml of water and 500 ml of chloroform. The chloroform layer was separated and dried over anhydrous magnesium sulfate. There was obtained from the chloroform solution upon concentration 13.8 g of ethyl 7-chloro-6-fluoro-1,4-dihydro-5-[(formyl)methylamino]-4-oxo-3-quinolinecarboxylate, m.p. 213°-216° C.

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 90 minutes
  2. customThe dimethylformamide was removed in high vacuum at 50° C.
  3. customthe residue was partitioned between 250 ml of water and 500 ml of chloroform
  4. customThe chloroform layer was separated
  5. dry with materialdried over anhydrous magnesium sulfate

Sources & evidence

ORD record
ord-e95da60994f24d97ad839b4f273b6b29
Source dataset
uspto-grants-1985_02
Patent number
US04499091

Reaction notes

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