4-(Hydroxyimino-methyl)-3-phenoxy-benzonitrile → 4-Aminomethyl-3-phenoxy-benzonitrile

HRID 1247346Notes

Reaction equation

HRID 1247346 reaction equation
O[N:2]=[CH:3][C:4]1[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[CH:6][C:5]=1[O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(O)(=O)C.[Zn]>[NH2:2][CH2:3][C:4]1[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[CH:6][C:5]=1[O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 1

HCID 865930434-(Hydroxyimino-methyl)-3-phenoxy-benzonitrile

Product 1

HCID 219056924-Aminomethyl-3-phenoxy-benzonitrileYield 87.6%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of 4-(hydroxyimino-methyl)-3-phenoxy-benzonitrile (200 mg) in acetic acid (1.2 ml) was stirred at 65° C. Zinc powder (500 mg) was added portionwise during 30 min. After stirring for a further 1 h, the reaction mixture was filtered and the filtrate was concentrated to near dryness. Water was added and the mixture was washed with diethyl ether. The organic phase was extracted (1×) with diluted acetic acid. The pH of the combined aqueous phases was adjusted to 11 using 2 N NaOH. The mixture was extracted with EtOAc. The organic phase was dried, filtered and concentrated to give 4-aminomethyl-3-phenoxy-benzonitrile (165 mg) as a light yellow oil.

Workup

  1. filtrationthe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. additionWater was added
  4. washthe mixture was washed with diethyl ether
  5. extractionThe organic phase was extracted (1×) with diluted acetic acid
  6. extractionThe mixture was extracted with EtOAc
  7. customThe organic phase was dried
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-0996f334f3a94fbfb76d35f4a8c0d1e5
Source dataset
uspto-grants-2006_10
Patent number
US07129238B2

Reaction notes

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