Sodium Sulfate → HCID 68829046, compound

HRID 1986413Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH2:12][CH:13]([CH3:15])[CH3:14])[C:6]([C:16](OC)=[O:17])=[C:5]2[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[H-].C([Al+]CC(C)C)C(C)C.S([O-])([O-])(=O)=O.[Na+].[Na+]>C1(C)C=CC=CC=1.O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH2:12][CH:13]([CH3:15])[CH3:14])[C:6]([CH2:16][OH:17])=[C:5]2[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

Conditions

Temperature: -75 °C

Procedure

To a solution of methyl 6-chloro-2-isobutyl-4-phenylquinoline-3-carboxylate (0.97 g, 2.74 mmol) in toluene (20 ml) was added 1.0 M solution (6.9 ml) of diisobutylaluminum hydride in toluene under a nitrogen atmosphere at −75° C. After stirring the mixture at −75° C. for 1 hr., a solution of sodium sulfate (0.97 g) in water (10 ml) was added. The temperature of the mixture was raised to room temperature and the mixture was further stirred for 1.5 hrs. Insoluble materials were removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography and crystallized from diisopropyl ether to give (6-chloro-2-isobutyl-4-phenylquinolin-3-yl)methanol (0.73 g, yield 82%) as colorless crystals.

Workup

temperatureThe temperature of the mixture was raised to room temperature
stirringthe mixture was further stirred for 1.5 hrs
customInsoluble materials were removed by filtration
concentrationthe filtrate was concentrated under reduced pressure
customThe residue was purified by silica gel column chromatography
customcrystallized from diisopropyl ether

Sources & evidence

ORD record: ord-4a31161cd43c49769a44dca3de496689
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07547710B2

Reaction notes

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