Sodium Bicarbonate → 1-(4-Chlorobenzoyl)-N-hydroxy-5-methoxy-2-methyl-1H-indole-3-methanamine

HRID 1461439

반응식

HRID 1461439 반응식
[Cl:1][C:2]1[CH:23]=[CH:22][C:5]([C:6]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([O:17][CH3:18])=[CH:14][CH:15]=3)[C:10](C=O)=[C:9]2[CH3:21])=[O:7])=[CH:4][CH:3]=1.[C:24]([BH3-])#[N:25].[Na+].C(=O)(O)[O-:29].[Na+]>C(O)(=O)C.C(OCC)(=O)C.C(Cl)Cl>[Cl:1][C:2]1[CH:23]=[CH:22][C:5]([C:6]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([O:17][CH3:18])=[CH:14][CH:15]=3)[C:10]([CH2:24][NH:25][OH:29])=[C:9]2[CH3:21])=[O:7])=[CH:4][CH:3]=1

참가 물질

7

반응물 3

HCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 108927871-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-carboxaldehyde

생성물 1

HCID 150273901-(4-Chlorobenzoyl)-N-hydroxy-5-methoxy-2-methyl-1H-indole-3-methanamine

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매2회

반응 조건

온도
0 °C

실험 절차

To a suspension of 1-(4-chlorobenzoyl)-5-methoxy-2-methyl-lH-indole-3-carboxaldehyde, oxime (1.0 g, 2.9 mmol) in 15 ml of acetic acid is added 0.9 g (14.6 mmol) of sodium cyanoborohydride (0.9 g, 14.6 mmol). The reaction mixture is stirred vigorously for three hours whereupon an additional 0.35 g (5.6 mmol) of the reducing agent is added. After an additional 45 minutes the reaction mixture is diluted with ethyl acetate and methylene chloride, cooled to 0° C., and 300 ml of a saturated solution of sodium bicarbonate is added dropwise while continuing to stir vigorously. This mixture is diluted further with 400 ml of ethyl acetate and separated from the aqueous phase (pH=9). The organic phase is washed again with a saturated solution of sodium bicarbonate, water, and finally a saturated solution of sodium chloride. It is dried over magnesium sulfate, filtered, and concentrated to a yellow oil which is crude 1-(4-chlorobenzoyl)-N-hydroxy-5-methoxy-2-methyl-lH-indole-3-methanamine and is used without further purification in the subsequent reaction. Mass balance is quantitative. A sample recrystallized from methylene chloride has a mp of 164°-165° C. (dec).

후처리

  1. additionis added
  2. stirringto stir vigorously
  3. customseparated from the aqueous phase (pH=9)
  4. washThe organic phase is washed again with a saturated solution of sodium bicarbonate, water
  5. dry with materialIt is dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated to a yellow oil which
  8. customis used without further purification in the subsequent reaction
  9. customA sample recrystallized from methylene chloride

출처 및 근거

ORD 기록
ord-fa75919616d44d4e940f5943f0741d6c
출처 데이터셋
uspto-grants-1991_12
특허 번호
US05075330

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