Aluminium lithium hydride → 1-{4-[2-(2-Hydroxymethylphenyl)benzoylamino]benzoyl}-1,2,3,4-tetrahydroquinoline

HRID 441251Notes

Reaction equation

C[O:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[CH:37]=[CH:36][CH:35]=[CH:34][C:12]=1[C:13]([NH:15][C:16]1[CH:33]=[CH:32][C:19]([C:20]([N:22]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH2:25][CH2:24][CH2:23]2)=[O:21])=[CH:18][CH:17]=1)=[O:14])=O.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[OH:2][CH2:3][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[CH:37]=[CH:36][CH:35]=[CH:34][C:12]=1[C:13]([NH:15][C:16]1[CH:33]=[CH:32][C:19]([C:20]([N:22]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH2:25][CH2:24][CH2:23]2)=[O:21])=[CH:18][CH:17]=1)=[O:14]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 1-{4-[2-(2-methoxycarbonylphenyl)benzoylamino]benzoyl}-1,2,3,4-tetrahydroquinoline (300 mg) and dry tetrahydrofuran (15 ml) was cooled to 0° C., and lithium aluminum hydride (46 mg) was added. The reaction mixture was maintained at 0° C. for 1 hour, and then was quenched by adding 1N hydrochloric acid. The resulting mixture was filtered through a bed of celite, diluted with ethyl acetate, washed with brine, dried over magnesium sulfate, and concentrated. Purification of the residue by column chromatography (silica gel, 15 g; ethyl acetate-n-hexane, 1:2) gave 1-{4-[2-(2-hydroxymethylphenyl)benzoylamino]benzoyl}-1,2,3,4-tetrahydroquinoline (80 mg) as a amorphous.

Workup

customwas quenched
additionby adding 1N hydrochloric acid
filtrationThe resulting mixture was filtered through a bed of celite
additiondiluted with ethyl acetate
washwashed with brine
dry with materialdried over magnesium sulfate
concentrationconcentrated
customPurification of the residue by column chromatography (silica gel, 15 g; ethyl acetate-n-hexane, 1:2)

Sources & evidence

ORD record: ord-99bffa4e641a4213851549c017c7024a
Source dataset: uspto-grants-1996_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05521170

Reaction notes

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