(Z)-2-amino-6-(prop-1-enyl)benzonitrile → 2-Amino-6-n-propylbenzonitrile

HRID 711745Notes

Reaction equation

HRID 711745 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6](/[CH:10]=[CH:11]\[CH3:12])[C:3]=1[C:4]#[N:5]>CCO.[Pd]>[NH2:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][CH2:11][CH3:12])[C:3]=1[C:4]#[N:5]

Participants

4

Reactant 1

HCID 67399331(Z)-2-amino-6-(prop-1-enyl)benzonitrile

Product 1

HCID 673998302-Amino-6-n-propylbenzonitrileYield 96%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

(Z)-2-Amino-6-(prop-1-enyl)benzonitrile (Example 131b) (0.45 g, 2.82 mmol) and 10% Pd/C (0.17 g) were stirred in EtOH (15 mL) under a hydrogen atmosphere for 4 h. The catalyst was filtered out, and the organic layer was concentrated under vacuum to give 0.43 g (96%) of 2-amino-6-n-propylbenzonitrile as yellow oil, which was used without further purification. MS 161 (MH+).

Workup

  1. filtrationThe catalyst was filtered out
  2. concentrationthe organic layer was concentrated under vacuum

Sources & evidence

ORD record
ord-300ef2b7a1b840a19b58dc55ee2c224b
Source dataset
uspto-grants-2015_11
Patent number
US09181276B2

Reaction notes

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