HCID 57197431, compound → HCID 22461140, compound

HRID 1857487Notes

Reaction equation

HRID 1857487 reaction equation
C(OC([N:11]1[C:20]2[C:15](=[CH:16][C:17]([F:25])=[C:18]([C:21]([F:24])([F:23])[F:22])[CH:19]=2)[C:14](=[O:26])[CH2:13][CH:12]1[CH3:27])=O)C1C=CC=CC=1>C(O)C.[Pd]>[F:25][C:17]1[CH:16]=[C:15]2[C:20](=[CH:19][C:18]=1[C:21]([F:22])([F:24])[F:23])[NH:11][CH:12]([CH3:27])[CH2:13][C:14]2=[O:26]

Participants

4

Reactant 1

HCID 57197431HCID 57197431, compound

Product 1

HCID 22461140HCID 22461140, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

6-Fluoro-2-methyl-4-oxo-7-trifluoromethyl-3,4-dihydro-2H-quinoline-1-carboxylic acid benzyl ester (3.0 g, 7.9 mmol) was combined with 250 mg of 10% Pd/C in 50 mL of ethanol and agitated under a hydrogen atmosphere (40 psi) for 1 hour before being filtered through Celite®, rinsing with ethyl acetate, and evaporating the volatiles under reduced pressure to afford 1.34 (69%) of the title compound as a colorless oil. 1H NMR (CDCl3) δ 1.4 (d, 3H), 2.5 (dd, 1H), 2.7 (dd, 1H), 3.7-3.9 (m, 1H), 4.4 (bs, 1H), 6.9 (d, 1H), 7.6 (d, 1H).

Workup

  1. filtrationbefore being filtered through Celite®
  2. washrinsing with ethyl acetate
  3. customevaporating the volatiles under reduced pressure

Sources & evidence

ORD record
ord-8a940fe7140647a397c7a2ef51d9a93c
Source dataset
uspto-grants-2000_11
Patent number
US06147090

Reaction notes

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