Methanol → HCID 20273174, 화합물

HRID 371500노트

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HRID 371500 반응식
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([C:18]1[CH:19]=[C:20]([CH:23]=[CH:24][CH:25]=1)[C:21]#[N:22])[CH2:13][CH2:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:26]([O-])(=[O:28])[CH3:27].[Na+].[H][H].CO>C(OC(=O)C)(=O)C.[Ni].CCOCC>[C:26]([NH:22][CH2:21][C:20]1[CH:23]=[CH:24][CH:25]=[C:18]([N:14]2[C:15]3[C:11](=[CH:10][C:9]([O:8][CH2:1][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)=[CH:17][CH:16]=3)[CH2:12][CH2:13]2)[CH:19]=1)(=[O:28])[CH3:27]

참가 물질

8

반응물 4

HCID 887MethanolHCID 517045Sodium AcetateHCID 133247163-(5-Benzyloxy-1-indolinyl)benzonitrileHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 20273174HCID 20273174, 화합물수율 86.8%

시약·촉매·용매 3

HCID 935Nickel촉매HCID 3283Diethyl Ether용매HCID 7918Acetic Anhydride용매

실험 절차

A solution of 1.52 g (4.7 mmole) of 3-(5-benzyloxy-1-indolinyl)benzonitrile of Example 18b in 60 ml acetic anhydride over 0.2 g Raney Nickel (#28 finely divided) and 0.76 g (9.3 mmole, 2 equivalents) sodium acetate was shaken at 50° C. under 50 psi of hydrogen until gas uptake had ceased and TLC analysis showed the reduction to be complete. The catalyst was filtered on a pad of celite and the filtrate was partitioned between chloroform (40 ml) and water (400 ml) and the combined organic portions were washed twice with water (600 ml), aqueous NaHCO3 (two 600 ml portions) and brine, dried over Na2SO4, and concentrated to give an oil. Chromatography on silica gel (80 g) using 1-5% methanol in ether afforded 1.31 g (86.8%) of N-Acetyl-3-(5-benzyloxy-1-indolinyl)benzenemethanamine as an oil.

후처리

  1. filtrationThe catalyst was filtered on a pad of celite
  2. customthe filtrate was partitioned between chloroform (40 ml) and water (400 ml)
  3. washthe combined organic portions were washed twice with water (600 ml), aqueous NaHCO3 (two 600 ml portions) and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customto give an oil

출처 및 근거

ORD 기록
ord-43eb213be6e2443297b393de5e2cb073
출처 데이터셋
uspto-grants-1985_07
특허 번호
US04532333

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