Aluminium lithium hydride → HCID 22117814, compound

HRID 1275823Notes

Reaction equation

CON(C)[C:4](=[O:17])[C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[C:7]([N:12]2[CH:16]=[CH:15][CH:14]=[CH:13]2)[CH:6]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[Cl:11][C:8]1[CH:9]=[CH:10][C:5]([CH:4]=[O:17])=[CH:6][C:7]=1[N:12]1[CH:16]=[CH:15][CH:14]=[CH:13]1

Participants

Conditions

Temperature: 2.5 °C

Procedure

A solution of 1.5 g of N-methoxy-N-methyl-4-chloro-3-(1H-pyrrol-1-yl)benzamide in 30 ml of anhydrous tetrahydrofuran was added drop-wise over a period of 30 minutes to a solution, pre-cooled to 0-5° C., of 237 mg of lithium aluminium hydride (98%) in 30 ml of anhydrous tetrahydrofuran. The mixture was stirred at 0-5° C. for a further 45 minutes and ther reaction was then quenched by the adition of 25 ml of saturated aqueous ammonium chloride solution and 25 ml of 50% aqueous hydro-chloric acid. The mixture was then extracted with three 100 ml portions of diethyl ether and the combined extracts were dried over anhydrous magnesium sulphate. The solvents were removed under reduced pressure and the residue was purified by column chromatography on silica gel using hexane/ethyl acetate (90:10) as the eluent to give 0.84 g of 4-chloro-3-(1H-pyrrol-1-yl)benzaldehyde as a yellow oil; nmr (CDC13, 250 Mhz) dH 10.00 (CHO).

Workup

customther reaction was then quenched by the adition of 25 ml of saturated aqueous ammonium chloride solution and 25 ml of 50% aqueous hydro-chloric acid
extractionThe mixture was then extracted with three 100 ml portions of diethyl ether
dry with materialthe combined extracts were dried over anhydrous magnesium sulphate
customThe solvents were removed under reduced pressure
customthe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record: ord-86a0b16299f34af69b7ce47540853a94
Source dataset: uspto-grants-2000_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06162918

Reaction notes

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