Cyclohexene → HCID 19851977, compound

HRID 1607153Notes

Reaction equation

HRID 1607153 reaction equation
[C:1]([C:4]1[CH:25]=[CH:24][C:7]([O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:20]=[CH:19][CH:18]=[C:17]([N+:21]([O-])=O)[C:14]=2[C:15]#[N:16])=[C:6]([CH2:26][CH2:27][CH3:28])[C:5]=1[OH:29])(=[O:3])[CH3:2].C1CCCCC=1>C(O)C.[Pd]>[NH2:21][C:17]1[CH:18]=[CH:19][CH:20]=[C:13]([O:12][CH2:11][CH2:10][CH2:9][O:8][C:7]2[CH:24]=[CH:25][C:4]([C:1](=[O:3])[CH3:2])=[C:5]([OH:29])[C:6]=2[CH2:26][CH2:27][CH3:28])[C:14]=1[C:15]#[N:16]

Participants

5

Reactant 2

HCID 8079CyclohexeneHCID 19851972HCID 19851972, compound

Product 1

HCID 19851977HCID 19851977, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

2.5 g of 10% palladium-on-carbon are added to a solution of 10 g (25.1 mmol) of 2-[3-(4-acetyl-3-hydroxy-2-propylphenoxy)-propoxy]-6-nitrobenzonitrile and 10 g of cyclohexene in 500 ml of ethanol and the whole is heated under reflux for 30 minutes. After cooling to room temperature the mixture is filtered and freed of solvent. Ether is added to the residue and the crystals that have separated out are filtered off. 2-amino-6-[3-(4-acetyl-3-hydroxy-2-n-propylphenoxy)-propoxy]-benzonitrile having a melting point of 120°-122° C. is obtained.

Workup

  1. temperaturethe whole is heated
  2. temperatureunder reflux for 30 minutes
  3. filtrationis filtered
  4. additionEther is added to the residue
  5. customthe crystals that have separated out
  6. filtrationare filtered off

Sources & evidence

ORD record
ord-85c6562642d843549930832fbc97d5fc
Source dataset
uspto-grants-1989_09
Patent number
US04863942

Reaction notes

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