Cornforth reagent → 3-(1-Nitro-2-naphthoyl)benzonitrile

HRID 1191303Notes

Reaction equation

HRID 1191303 reaction equation
[OH:1][CH:2]([C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]=1[N+:21]([O-:23])=[O:22])[C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[C:6]#[N:7].[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>ClCCl>[N+:21]([C:12]1[C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:19]=[CH:20][C:11]=1[C:2]([C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[C:6]#[N:7])=[O:1])([O-:23])=[O:22]

Participants

4

Reactant 2

HCID 2724130Cornforth reagentHCID 866904453-[Hydroxy(1-nitronaphthalen-2-yl)methyl]benzonitrile

Product 1

HCID 866904463-(1-Nitro-2-naphthoyl)benzonitrileYield 86.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-[hydroxy(1-nitronaphthalen-2-yl)methyl]benzonitrile (7.37 g, 24.2 mmol) in dichloromethane (70 mL) was added silica gel (30 g) and pyridinium dichromate (13.7 g, 36.3 mmol), and stirred for 18 hours. The reaction mixture was filtered, and the residue was washed with chloroform. The filtrate was concentrated to dryness, and the residue was recrystallized from ethyl acetate, and washed with hexane to give the titled compound as a pale yellow crystal (6.32 g, yield 86%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. washthe residue was washed with chloroform
  3. concentrationThe filtrate was concentrated to dryness
  4. customthe residue was recrystallized from ethyl acetate
  5. washwashed with hexane

Sources & evidence

ORD record
ord-1419e081f6a949c6aec4ed7feba67278
Source dataset
uspto-grants-2014_03
Patent number
US08680110B2

Reaction notes

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