Potassium Carbonate → HCID 20067132, compound

HRID 561137Notes

Reaction equation

HRID 561137 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([O:13][CH3:14])[C:11]=1[F:12])[NH:8][CH:7]=[C:6]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:5]2=[O:20].[C:21]([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:21][N:8]1[C:9]2[C:4](=[CH:3][C:2]([F:1])=[C:11]([F:12])[C:10]=2[O:13][CH3:14])[C:5](=[O:20])[C:6]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:7]1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 20067141HCID 20067141, compound

Product 1

HCID 20067132HCID 20067132, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of ethyl 6,7-difluoro-1,4-dihydro-8-methoxy-4-oxoquinoline-3-carboxylate (1.00 g, 3.53 mmol), iodomehtane (0.450 mL, 7.23 mmol) and K2CO3 (976 mg, 7.06 mmol) in DMF (15 mL) was heated at 50° C. for 1 h. The mixture was concentrated in vacuo and dried under high vacuum. The reaction mixture was poured into ice water and the resulting precipitate was removed by filtration, washed with water and then dried to yield ethyl 1-methyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxoquinoline-3-carboxylate (845 mg, 81%) as a colorless solid.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customdried under high vacuum
  3. additionThe reaction mixture was poured into ice water
  4. customthe resulting precipitate was removed by filtration
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-8d6ab11e98324acc8b79c9c8410d1eea
Source dataset
uspto-grants-2011_11
Patent number
US08063221B2

Reaction notes

Loading…