HCID 178471909, compound → Ethyl 1-cyclopentyl-6,7-difluoro-8-methoxy-1,4-dihydro-4-oxoquinoline-3-carboxylate

HRID 561098Notes

Reaction equation

HRID 561098 reaction equation
[CH3:1][O:2][C:3]1[C:4](F)=[C:5]([CH:21]=[C:22]([F:25])[C:23]=1[F:24])[C:6]([C:8](=[CH:14][NH:15][CH:16]1[CH2:20][CH2:19][CH2:18][CH2:17]1)[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[O:7]>C1COCC1.C(O[K])(C)(C)C>[CH:16]1([N:15]2[C:4]3[C:5](=[CH:21][C:22]([F:25])=[C:23]([F:24])[C:3]=3[O:2][CH3:1])[C:6](=[O:7])[C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:14]2)[CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

4

Reactant 1

HCID 178471909HCID 178471909, compound

Product 1

HCID 57794160Ethyl 1-cyclopentyl-6,7-difluoro-8-methoxy-1,4-dihydro-4-oxoquinoline-3-carboxylateYield 69.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 178418922HCID 178418922, compoundSolvent

Procedure

To a solution of 14 (9.5 g, 25 mmol) in THF (100 mL), 1M tBuOK in THF (25 mL, 25 mmol) was added dropwise under ice-cooling. After 1.5 h, the reaction mixture was poured into ice-water (20 mL) and the product extracted with CH2Cl2 (3×20 mL). After evaporation of the solvent, 15 was obtained as an orange solid (6.1 g, 69%)

Workup

  1. temperaturecooling
  2. extractionthe product extracted with CH2Cl2 (3×20 mL)
  3. customAfter evaporation of the solvent

Sources & evidence

ORD record
ord-05bd11d8c05242ebbd4aedf6c707c49a
Source dataset
uspto-grants-2011_11
Patent number
US08063221B2

Reaction notes

Loading…