Cyclohexene → (2-Amino-5-hydroxyphenyl)acetonitrile

HRID 1941534Notes

Reaction equation

HRID 1941534 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10]CC2C=CC=CC=2)=[CH:6][C:5]=1[CH2:18][C:19]#[N:20])([O-])=O.C1CCCCC=1>[Pd].C(O)C>[C:19]([CH2:18][C:5]1[CH:6]=[C:7]([OH:10])[CH:8]=[CH:9][C:4]=1[NH2:1])#[N:20]

Participants

5

Reactant 2

HCID 8079CyclohexeneHCID 14025389HCID 14025389, compound

Product 1

HCID 19607200(2-Amino-5-hydroxyphenyl)acetonitrile

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of 5.4 g of 2-nitro 5-benzyloxyphenylacetonitrile, 5.4 ml of cyclohexene, 22 ml of ethanol and 3 g of 10% palladium on activated charcoal was refluxed for five hours. The suspension was then hot filtered and the filtrate evaporated. The residue was recrystallised from ethanol to produce dark beige crystals.

Workup

  1. temperaturewas refluxed for five hours
  2. filtrationThe suspension was then hot filtered
  3. customthe filtrate evaporated
  4. customThe residue was recrystallised from ethanol
  5. customto produce dark beige crystals

Sources & evidence

ORD record
ord-9f85d6aa879d4d139c24221fd3f34af8
Source dataset
uspto-grants-1997_12
Patent number
US05703266

Reaction notes

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