HCID 59002969, compound → HCID 20067141, compound

HRID 561136Notes

Reaction equation

HRID 561136 reaction equation
C([N:5]1[C:14]2[C:9](=[CH:10][C:11]([F:18])=[C:12]([F:17])[C:13]=2[O:15][CH3:16])[C:8](=[O:19])[C:7]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:6]1)(C)(C)C>C(Cl)Cl.FC(F)(F)C(O)=O>[F:18][C:11]1[CH:10]=[C:9]2[C:14](=[C:13]([O:15][CH3:16])[C:12]=1[F:17])[NH:5][CH:6]=[C:7]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:8]2=[O:19]

Participants

4

Reactant 1

HCID 59002969HCID 59002969, compound

Product 1

HCID 20067141HCID 20067141, compoundYield 99.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of ethyl 1-tert-butyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxoquinoline-3-carboxylate (4.00 g, 11.8 mmol) in CH2Cl2 (20 mL) and trifluoroacetic acid (4.0 mL) was stirred at 0° C. for 30 min. The mixture was concentrated in vacuo and poured into 500 mL of ice-water. The resulting precipitate was removed by filtration, washed with water and then dried to yield ethyl 6,7-difluoro-1,4-dihydro-8-methoxy-4-oxoquinoline-3-carboxylate (3.34 g, quant) as a colorless solid.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. additionpoured into 500 mL of ice-water
  3. customThe resulting precipitate was removed by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-b124b027804a41adbfd7d2e0f6e22e98
Source dataset
uspto-grants-2011_11
Patent number
US08063221B2

Reaction notes

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