Cyclohexene → HCID 19818639, compound

HRID 652325Notes

Reaction equation

HRID 652325 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][C:28]([F:31])([F:30])[F:29])[C:5]=1[OH:32])(=[O:3])[CH3:2].C1CCCCC=1>C(O)C>[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:32])[C:6]=2[CH2:26][CH2:27][C:28]([F:29])([F:30])[F:31])[C:14]=1[C:15]#[N:16]

Participants

4

Reactant 2

HCID 8079CyclohexeneHCID 19818592HCID 19818592, compound

Product 1

HCID 19818639HCID 19818639, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2.5 g of 10% Pd-on-charcoal are added to a solution of 10 g of 2-{3-[4-acetyl-3-hydroxy-2-(3,3,3-trifluoropropyl)-phenoxy]-propoxy}-6-nitro-benzonitrile and 10 g of cyclohexene in 500 ml of ethanol and the mixture is refluxed for 30 minutes. After cooling to room temperature, it is filtered and freed from the solvent. Ether is added to the residue and the crystals which have separated out are filtered off. 2-Amino-6-{-3-[4-acetyl-3-hydroxy-2-(3,3,3-trifluoropropyl)-phenoxy]-propoxy}-benzonitrile is obtained.

Workup

  1. temperaturethe mixture is refluxed for 30 minutes
  2. filtrationit is filtered
  3. additionEther is added to the residue
  4. customthe crystals which have separated out
  5. filtrationare filtered off

Sources & evidence

ORD record
ord-87216da6561945e889a1067a0e5e6522
Source dataset
uspto-grants-1987_06
Patent number
US04670604

Reaction notes

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