Potassium Acetate → 5-amino-3,4-dihydro-4-hydroxy-4-(trifluoromethyl)-1H-quinolin-2-one

HRID 1350132Notes

Reaction equation

HRID 1350132 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10](Cl)[CH:9]=[C:8]2[C:3]=1[C:4]([OH:18])([C:14]([F:17])([F:16])[F:15])[CH2:5][C:6](=[O:13])[NH:7]2.CC([O-])=O.[K+]>C(O)C.[Pd]>[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4]([OH:18])([C:14]([F:17])([F:15])[F:16])[CH2:5][C:6](=[O:13])[NH:7]2

Participants

5

Reactant 2

HCID 517044Potassium AcetateHCID 222791795-amino-7-chloro-3,4-dihydro-4-hydroxy-4-(trifluoromethyl)-1H-quinolin-2-one

Product 1

HCID 210943795-amino-3,4-dihydro-4-hydroxy-4-(trifluoromethyl)-1H-quinolin-2-oneYield 101.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 5-amino-7-chloro-3,4-dihydro-4-hydroxy-4-(trifluoromethyl)-1H-quinolin-2-one (8.0 g, 28 mmol), KOAc (5.6 g, 57 mmol) and 10% Pd—C (4.0 g) in 200 mL ethanol was stirred under an atmosphere of hydrogen for 2 h. The mixture was filtered through Celite and concentrated under reduced pressure. The resultant solid was dissolved in EtOAc (250 mL) and washed sequentially with saturated NaHCO3 (200 mL) and brine (200 mL), dried over MgSO4, filtered and concentrated to afford 7.0 g (100%) of 5-amino-3,4-dihydro-4-hydroxy-4-(trifluoromethyl)-1H-quinolin-2-one, a foamy tan solid. 1H NMR (400 MHz, acetone-d6) δ 9.16 (broad s, 1H), 6.99 (t, 1H, J=8.0), 6.44 (broad s, 1H), 6.39 (d, 1H, J=7.9), 6.26 (d, 1H, J=7.9), 5.44 (broad s, 2H), 3.09 (d, AB, J=17.0), 2.93 (d, AB, J=17.0).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe resultant solid was dissolved in EtOAc (250 mL)
  4. washwashed sequentially with saturated NaHCO3 (200 mL) and brine (200 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-140177cda5c342e59c274f1aebd6704f
Source dataset
uspto-grants-2007_05
Patent number
US07214690B2

Reaction notes

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