Methanol → 2-(2-Oxo-6-(trifluoromethyl)-3,4-dihydroquinolin-1(2H)-yl)acetic acid

HRID 1519885Notes

Reaction equation

HRID 1519885 reaction equation
[O:1]=[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:12]([F:15])([F:14])[F:13])[CH:8]=2)[N:3]1[CH2:16][C:17]([OH:19])=[O:18].CO>[Pd]>[O:1]=[C:2]1[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:12]([F:14])([F:13])[F:15])[CH:8]=2)[N:3]1[CH2:16][C:17]([OH:19])=[O:18]

Participants

4

Reactant 2

HCID 887MethanolHCID 687598572-(2-oxo-6-(trifluoromethyl)quinolin-1(2H)-yl)acetic acid

Product 1

HCID 687846172-(2-Oxo-6-(trifluoromethyl)-3,4-dihydroquinolin-1(2H)-yl)acetic acid

Reagents, catalysts & solvents 1

HCID 23938PalladiumSolvent

Procedure

To a stirring mixture of 2-(2-oxo-6-(trifluoromethyl)quinolin-1(2H)-yl)acetic acid in Pd/C was added MeOH. The reaction mixture was placed under an atmosphere of hydrogen (balloon) for several hours. The product mixture was filtered through a plug of celite. The plug was washed several times with EtOAc. The mixture was concentrated under reduced pressure and the crude amine was taken directly to the next reaction without further purification. Retention time (min)=1.841, method [1], MS(ESI) 274.1 (M+H).

Workup

  1. waitThe reaction mixture was placed under an atmosphere of hydrogen (balloon) for several hours
  2. filtrationThe product mixture was filtered through a plug of celite
  3. washThe plug was washed several times with EtOAc
  4. concentrationThe mixture was concentrated under reduced pressure
  5. customthe crude amine was taken directly to the next reaction without further purification

Sources & evidence

ORD record
ord-bb89b681c2364855a8ce3f48f5eb1308
Source dataset
uspto-grants-2015_07
Patent number
US09073891B2

Reaction notes

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