Sodium Sulfate → HCID 68829518, compound

HRID 1986416Notes

Reaction equation

[Br: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>[Br: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-bromo-2-isobutyl-4-phenylquinoline-3-carboxylate (3.0 g, 7.5 mmol) in toluene (100 ml) was added 0.95 M solution (20 ml) of diisobutylaluminum hydride in toluene at −75° C. under a nitrogen atmosphere. After stirring the mixture at −75° C. for 1 hr., a solution of sodium sulfate (2.7 g) in water (15 ml) was added. The temperature of the mixture was raised to room temperature and the mixture was further stirred for 1 hr. Insoluble materials were removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was crystallized from n-hexane, and recrystallized from n-hexane-toluene to give (6-bromo-2-isobutyl-4-phenylquinolin-3-yl)methanol (1.6 g, yield 57%) as pale-yellow crystals.

Workup

temperatureThe temperature of the mixture was raised to room temperature
stirringthe mixture was further stirred for 1 hr
customInsoluble materials were removed by filtration
concentrationthe filtrate was concentrated under reduced pressure
customThe residue was crystallized from n-hexane
customrecrystallized from n-hexane-toluene

Sources & evidence

ORD record: ord-efc441b6fdc84b5a9ca9f4413729da17
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07547710B2

Reaction notes

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