Aluminium lithium hydride → (6-Bromo-4-methylquinolin-2-yl)methanol

HRID 734853Notes

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].[Br:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[N:14]=[C:13]([C:18](OC)=[O:19])[CH:12]=[C:11]2[CH3:22]>C1COCC1.CCOC(C)=O>[Br:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[N:14]=[C:13]([CH2:18][OH:19])[CH:12]=[C:11]2[CH3:22]

Participants

Conditions

Temperature: 0 °C

Procedure

Under a nitrogen atmosphere at 0C, 1.50 mL (1.50 mmol) of a lithium aluminum hydride solution (1M in THF) was slowly added to a solution of 0.65 g (2.32 mmol) of methyl 6-bromo-4-methylquinoline-2-carboxylate in 30 mL of THF and the mixture was stirred for 30 minutes at 0° C. A further 0.25 mL of lithium aluminum hydride solution (1M in THF) was added and the mixture was stirred for 20 minutes at 0° C. The reaction mixture was combined with a few drops of EtOAc, worked up using the Fieser-Fieser method, and the precipitate was filtered off and washed with EtOAc. The filtrate was evaporated down in vacuo. Yield: 0.25 g (43% of theoretical); C11H10BrNO (M=252.107); calc.: molpeak (M+H)+: 252/254 (Br); found: molpeak (M+H)+: 252/254 (Br); Rf value: 0.25 (silica gel, PE/EtOAc 3:2).

Workup

stirringthe mixture was stirred for 20 minutes at 0° C
filtrationthe precipitate was filtered off
washwashed with EtOAc
customThe filtrate was evaporated down in vacuo

Sources & evidence

ORD record: ord-e330c98984114680b347deabb190ee45
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07592358B2

Reaction notes

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