Methanol → HCID 20273174, compound

HRID 371500Notes

Reaction equation

HRID 371500 reaction equation
[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]

Participants

8

Reactant 4

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

Product 1

HCID 20273174HCID 20273174, compoundYield 86.8%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 3283Diethyl EtherSolventHCID 7918Acetic AnhydrideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-43eb213be6e2443297b393de5e2cb073
Source dataset
uspto-grants-1985_07
Patent number
US04532333

Reaction notes

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