Water → HCID 21220308, compound

HRID 1584816Notes

Reaction equation

HRID 1584816 reaction equation
[Br:1][C:2]1[C:20]([F:21])=[CH:19][C:5]([C:6]([C:8](=[CH:14][NH:15][CH:16]2[CH2:18][CH2:17]2)[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[O:7])=[C:4](F)[C:3]=1[CH3:23].C(=O)([O-])[O-].[K+].[K+].O>CS(C)=O>[Br:1][C:2]1[C:3]([CH3:23])=[C:4]2[C:5]([C:6](=[O:7])[C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:14][N:15]2[CH:16]2[CH2:18][CH2:17]2)=[CH:19][C:20]=1[F:21]

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 178471861HCID 178471861, compound

Product 1

HCID 21220308HCID 21220308, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

In 175 ml of dimethyl sulfoxide was dissolved 35.0 g of ethyl 2-(4-bromo-2,5-difluoro-3-methylbenzoyl)-3-cyclopropylaminoacrylate, and 27.4 g of potassium carbonate was added to the solution, after which the resulting mixture was stirred at 100° C. for 30 minutes. The reaction mixture was cooled to room temperature, and 1,000 ml of water was then added thereto, after which the crystals formed were collected by filtration, to obtain 30.0 g of colorless, crystalline ethyl 7-bromo-1-cyclopropyl-6-fluoro-8-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylate.

Workup

  1. additionwas added to the solution
  2. temperatureThe reaction mixture was cooled to room temperature
  3. customafter which the crystals formed
  4. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-ff799f89d2c648c1a90fc65a51119b63
Source dataset
uspto-grants-1999_08
Patent number
US05935952

Reaction notes

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