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

HRID 441251
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HRID 441251 반응식
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]
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참가 물질

4

반응물 2

HCID 21226445Aluminium lithium hydrideHCID 224051041-{4-[2-(2-Methoxycarbonylphenyl)benzoylamino]benzoyl}-1,2,3,4-tetrahydroquinoline

생성물 1

HCID 224052581-{4-[2-(2-Hydroxymethylphenyl)benzoylamino]benzoyl}-1,2,3,4-tetrahydroquinoline수율 28.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-99bffa4e641a4213851549c017c7024a
출처 데이터셋
uspto-grants-1996_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05521170

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