Hydrochloric Acid → HCID 58026983, compound

HRID 909331Notes

Reaction equation

HRID 909331 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:17])[CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:5][C:4]=1[C:18]1[C:19]([CH2:31][O:32][C:33](=[O:41])[C:34]2[CH:39]=[CH:38][C:37]([CH3:40])=[CH:36][CH:35]=2)=[C:20]2[C:25](=[CH:26][CH:27]=1)[NH:24][C:23]([CH3:29])([CH3:28])[CH:22]=[C:21]2[CH3:30].[BH4-].[Na+].Cl.C(OCC)(=O)C>O1CCCC1.CO>[OH:17][CH:9]([C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[C:4]([C:18]2[C:19]([CH2:31][O:32][C:33](=[O:41])[C:34]3[CH:35]=[CH:36][C:37]([CH3:40])=[CH:38][CH:39]=3)=[C:20]3[C:25](=[CH:26][CH:27]=2)[NH:24][C:23]([CH3:29])([CH3:28])[CH:22]=[C:21]3[CH3:30])[CH:5]=1)[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 58026943HCID 58026943, compound

Product 1

HCID 58026983HCID 58026983, compoundYield 93.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

6-(2-Methoxy-5-phenylacetylphenyl)-5-(4-methylbenzoyloxymethyl)-2,2,4-trimethyl -1,2-dihydroquinoline (Compound No. 22, 34.0 mg. 0.0623 mmol) was dissolved in tetrahydrofuran (0.5 mL)—methanol (0.5 mL), and sodium borohydride (6.8 mg, 0.180 mmol) was added thereto, and then the reaction mixture was stirred at room temperature for 45 minutes. 1N aqueous HCl solution (0.5 mL) and ethyl acetate (50 mL) were added to the reaction mixture, the whole was washed with water (50 mL, twice) and saturated brine (50 mL) successively, dried over anhydrous magnesium sulfate, and then the solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give the titled compound (31.8 mg) as a colorless amorphous product. (yield: 93%)

Workup

  1. additionwas added
  2. washthe whole was washed with water (50 mL
  3. dry with materialtwice) and saturated brine (50 mL) successively, dried over anhydrous magnesium sulfate
  4. customthe solvent was removed under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-5bd9b0744a704e4e8b006438524ec50d
Source dataset
uspto-grants-2011_09
Patent number
US08017775B2

Reaction notes

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