Trifluoroacetic acid → HCID 67441923, compound

HRID 1800934Notes

Reaction equation

HRID 1800934 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[CH:13]=1)[C:6]([CH3:22])([CH3:21])[CH:5]2O.FC(F)(F)C(O)=O>C([SiH](CC)CC)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[CH:13]=1)[C:6]([CH3:22])([CH3:21])[CH2:5]2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67441468HCID 67441468, compound

Product 1

HCID 67441923HCID 67441923, compoundYield 77.1%

Reagents, catalysts & solvents 1

HCID 12052TriethylsilaneSolvent

Conditions

Temperature
25 °C

Procedure

To a mixture of 6-chloro-3,3-dimethyl-2-(3-nitro-phenyl)-1,2,3,4-tetrahydro-quinolin-4-ol (14.3 g, 43 mmol) and triethylsilane (20 mL) at 25° C. was added trifluoroacetic acid (5 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) to afford 6-chloro-3,3-dimethyl-2-(3-nitro-phenyl)-1,2,3,4-tetrahydro-quinoline (10.5 g, 77%) as a white solid: LC/MS m/e calcd for C17H17ClN2O2 (M+H)+: 317.79, observed: 317.0.

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-5ff2ea6db7e040e6a04a528606f93b14
Source dataset
uspto-grants-2013_01
Patent number
US08344137B2

Reaction notes

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