Trifluoroacetic acid → HCID 67441792, compound

HRID 1800876Notes

Reaction equation

HRID 1800876 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([Cl:27])[CH:8]=[C:9]2[C:14]=1[NH:13][CH:12]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([N+:21]([O-:23])=[O:22])[CH:16]=1)[C:11]([CH3:25])([CH3:24])[CH:10]2O)=[O:4].FC(F)(F)C(O)=O>C([SiH](CC)CC)C>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([Cl:27])[CH:8]=[C:9]2[C:14]=1[NH:13][CH:12]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([N+:21]([O-:23])=[O:22])[CH:16]=1)[C:11]([CH3:24])([CH3:25])[CH2:10]2)=[O:4]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67442746HCID 67442746, compound

Product 1

HCID 67441792HCID 67441792, compoundYield 13.3%

Reagents, catalysts & solvents 1

HCID 12052TriethylsilaneSolvent

Conditions

Temperature
25 °C

Procedure

To a mixture of 6-chloro-4-hydroxy-3,3-dimethyl-2-(3-nitro-phenyl)-1,2,3,4-tetrahydro-quinoline-8-carboxylic acid methyl ester (7.8 g, 20 mmol) and triethylsilane (30 mL) at 25° C. was added trifluoroacetic acid (15 mL) dropwise. The resulting mixture was stirred at 25° C. for 1 h. Then the reaction mixture was concentrated in vacuo and the residue was extracted with ethyl acetate (2×200 mL), washed with saturated aqueous sodium bicarbonate solution (2×100 mL), dried over anhydrous sodium sulfate and concentrated in vacuo. Purification on flash silica gel chromatography (silica gel from QingDao, 200-300 mesh, glass column from Shanghai SD company) (10% ethyl acetate/hexanes) afforded 6-chloro-3,3-dimethyl-2-(3-nitro-phenyl)-1,2,3,4-tetrahydro-quinoline-8-carboxylic acid methyl ester (1 g, 13%) as a white solid: LC/MS m/e calcd for C19H19ClN2O4 (M+H)+: 375.83, observed: 375.1.

Workup

  1. concentrationThen the reaction mixture was concentrated in vacuo
  2. extractionthe residue was extracted with ethyl acetate (2×200 mL)
  3. washwashed with saturated aqueous sodium bicarbonate solution (2×100 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customPurification on flash silica gel chromatography (silica gel from QingDao, 200-300 mesh, glass column from Shanghai SD company) (10% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-ce152c2bfaae4885811e784054c7f5a7
Source dataset
uspto-grants-2013_01
Patent number
US08344137B2

Reaction notes

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