Ammonia → (+-)-Cicloprofen

HRID 1729897Notes

Reaction equation

HRID 1729897 reaction equation
[CH3:1][CH:2]([C:5]1[CH:17]=[CH:16][C:15]2[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH2:8][C:7]=2[CH:6]=1)[C:3]#N.[OH-:18].[K+].N.C([OH:23])C>>[CH3:1][CH:2]([C:5]1[CH:17]=[CH:16][C:15]2[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH2:8][C:7]=2[CH:6]=1)[C:3]([OH:23])=[O:18]

Participants

5

Reactant 4

HCID 222AmmoniaHCID 702EthanolHCID 14797Potassium HydroxideHCID 21406512HCID 21406512, compound

Product 1

HCID 37589(+-)-Cicloprofen

Procedure

2.1g. of α-methylfluorene-2-acetonitrile is refluxed in 60% aqueous ethanol (50ml.) containing potassium hydroxide (5g.) until the evolution of ammonia ceases. The ethanol is evaporated and the aqueous solution acidified to pH 2.0 with HCl and extracted with ether. The ether extracts are washed with water, dried (MgSO4) and evaporated to give the title compound.

Workup

  1. customThe ethanol is evaporated
  2. extractionextracted with ether
  3. washThe ether extracts are washed with water
  4. dry with materialdried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-78f597590cd04d3da500a442173e15af
Source dataset
uspto-grants-1976_11
Patent number
US03989841

Reaction notes

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