Acetic Anhydride → 2-Cyano-4'-methylbiphenyl

HRID 494343Notes

Reaction equation

HRID 494343 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([CH:14]=O)=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:4][CH:3]=1.Cl.O[NH2:18].C(OC(=O)C)(=O)C>N1C=CC=CC=1>[C:14]([C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[C:5]1[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=1)#[N:18]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 443297Hydroxyamine hydrochlorideHCID 13940094'-Methyl[1,1'-biphenyl]-2-carbaldehyde

Product 1

HCID 1455122-Cyano-4'-methylbiphenylYield 79%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 4′-methyl-2-biphenylcarbaldehyde (2.0 g) and hydroxyamine hydrochloride (1.0 g) in pyridine (10 ml) was stirred at room temperature for 15 min., followed by addition of acetic anhydride (4.1 g). The reaction mixture was stirred at 90-100° C. for 1 hr. and concentrated to dryness. After addition of water to the residue, the precipitated crystals were collected by filtration. Recrystallization from hexane gave colorless needles (1.5 g, 79%).

Workup

  1. stirringThe reaction mixture was stirred at 90-100° C. for 1 hr
  2. concentrationand concentrated to dryness
  3. additionAfter addition of water to the residue
  4. filtrationthe precipitated crystals were collected by filtration
  5. customRecrystallization from hexane

Sources & evidence

ORD record
ord-43f7537f71924457978d082e87fe6051
Source dataset
uspto-grants-2009_05
Patent number
US07538133B2

Reaction notes

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