Formic Acid → 5-Hydroxymethyl-6-phenyl-2,2,4-trimethyl-1,2-dihydroquinoline

HRID 1966282Notes

Reaction equation

HRID 1966282 reaction equation
[OH:1][CH2:2][C:3]1[C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2OS(C(F)(F)F)(=O)=O)=[CH:11][CH:10]=[C:9]2[C:4]=1[C:5]([CH3:29])=[CH:6][C:7]([CH3:28])([CH3:27])[NH:8]2.C(N(CC)CC)C.C(O)=O>CN(C)C=O.C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[OH:1][CH2:2][C:3]1[C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:11][CH:10]=[C:9]2[C:4]=1[C:5]([CH3:29])=[CH:6][C:7]([CH3:28])([CH3:27])[NH:8]2

Participants

7

Reactant 3

HCID 284Formic AcidHCID 8471TriethylamineHCID 584854825-Hydroxymethyl-6-(2-trifluoromethylsulfonyloxyphenyl)-2,2,4-trimethyl-1,2-dihydroquinoline

Product 1

HCID 580267805-Hydroxymethyl-6-phenyl-2,2,4-trimethyl-1,2-dihydroquinoline

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

5-Hydroxymethyl-6-(2-trifluoromethylsulfonyloxyphenyl)-2,2,4-trimethyl-1,2-dihydroquinoline (Reference Compound No. 6-1, 136 mg, 0.318 mmol) was dissolved in anhydrous N,N-dimethylformamide (1.5 mL), then the solvent was bubbled with argon for 2 minutes, and then tetrakis(triphenylphosphine)palladium(0) (35.6 mg, 0.0308 mmol), triethylamine (221 μL, 1.59 mmol) and formic acid (60 μL, 1.6 mmol) were added thereto. After the reaction mixture was stirred at 60° C. for 10 hours, it was diluted with ethyl acetate (50 mL). The whole was washed with saturated NaHCO3 solution (30 mL) and saturated brine (30 mL) successively, dried over anhydrous magnesium sulfate, and then the solvent was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give the titled reference compound (93.0 mg) as a yellow oil. (quantative)

Workup

  1. customthe solvent was bubbled with argon for 2 minutes
  2. washThe whole was washed with saturated NaHCO3 solution (30 mL) and saturated brine (30 mL) successively
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was removed under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-08a6d1858ac5446bad50ae03fbcac866
Source dataset
uspto-grants-2013_04
Patent number
US08420635B2

Reaction notes

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