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Hydroxyamine hydrochloride → 1-cyclohexylmethyl-7-methoxy-1H-indole-3-carbaldehyde oxime

HRID 644069
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HRID 644069 반응식
[CH:1]1([CH2:7][N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][C:15]=3[O:17][CH3:18])[C:10]([CH:19]=O)=[CH:9]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.[NH2:22][OH:23].C([O-])(=O)C.[Na+]>C(O)C.O>[CH:1]1([CH2:7][N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][C:15]=3[O:17][CH3:18])[C:10]([CH:19]=[N:22][OH:23])=[CH:9]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1
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참가 물질

6

반응물 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 860732881-(cyclohexyl)methyl-7-methoxy-1H-indole-3-carbaldehyde

생성물 1

HCID 860732891-cyclohexylmethyl-7-methoxy-1H-indole-3-carbaldehyde oxime수율 44.8%

시약·촉매·용매 2

HCID 702Ethanol용매
HCID 962
Water
용매

실험 절차

To a solution of 1-(cyclohexyl)methyl-7-methoxy-1H-indole-3-carbaldehyde (780 mg, 2.9 mmol) in a mixture of ethanol (8 ml) and water (2 ml) was added hydroxylamine hydrochloride (403 mg, 5.8 mmol) and sodium acetate (713 mg, 8.7 mmol) and the solution stirred for 64 h at room temperature. The mixture was concentrated in vacuo and the residue diluted with water (50 ml) and extracted with ethyl acetate (3×50 ml). The product was recrystallised from diethyl ether/hexane to yield 1-cyclohexylmethyl-7-methoxy-1H-indole-3-carbaldehyde oxime (380 mg, 1.3 mmol) as a yellow powder.

후처리

  1. concentrationThe mixture was concentrated in vacuo
  2. additionthe residue diluted with water (50 ml)
  3. extractionextracted with ethyl acetate (3×50 ml)
  4. customThe product was recrystallised from diethyl ether/hexane

출처 및 근거

ORD 기록
ord-9a204dc13a684b9faaa02ef2174d2016
출처 데이터셋
uspto-grants-2010_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07700634B2

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