Acetic Anhydride → 2-Cyano-4'-methylbiphenyl

HRID 860935Notes

Reaction equation

HRID 860935 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-c65a662b03914d07a8d045675fc45f51
Source dataset
uspto-grants-2006_12
Patent number
US07153972B2

Reaction notes

Loading…