Water → 2-(5,5-ethylenedioxy-5H-dibenzo[a,d]cyclohepten-2-yl)propionamide

HRID 1576178Notes

Reaction equation

HRID 1576178 reaction equation
[CH2:1]1[CH2:23][O:22][C:3]2([C:9]3[CH:10]=[CH:11][C:12]([CH:14]([CH3:17])[C:15]#[N:16])=[CH:13][C:8]=3[CH:7]=[CH:6][C:5]3[CH:18]=[CH:19][CH:20]=[CH:21][C:4]2=3)[O:2]1.[OH2:24].[OH-].[K+]>CO>[CH2:23]1[CH2:1][O:2][C:3]2([C:9]3[CH:10]=[CH:11][C:12]([CH:14]([CH3:17])[C:15]([NH2:16])=[O:24])=[CH:13][C:8]=3[CH:7]=[CH:6][C:5]3[CH:18]=[CH:19][CH:20]=[CH:21][C:4]2=3)[O:22]1

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 214031012-(5,5-ethylenedioxy-5H-dibenzo[a,d]cyclohepten-2-yl)propionitrile

Product 1

HCID 214030982-(5,5-ethylenedioxy-5H-dibenzo[a,d]cyclohepten-2-yl)propionamideYield 57%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3.0 Gm. of 2-(5,5-ethylenedioxy-5H-dibenzo[a,d]cyclohepten-2-yl)propionitrile is refluxed for 3 hours in 50 ml. of water and 10 ml. of methanol containing 0.55 gm. of potassium hydroxide. The solution is cooled and extracted with ethyl acetate. The extract is washed with aqueous sodium carbonate and water, then dried and evaporated to yield 57% of 2-(5,5-ethylenedioxy-5H-dibenzo[a,d]cyclohepten-2-yl)propionamide. Use of 2-(5,5-ethylenedioxy-5H-dibenzo[a,d]cyclohepten-2-yl) acetonitrile and a one hour reaction time gives a similar yield of 2-(5,5-ethylenedioxy-5H-dibenzo[a,d]cyclohepten-2-yl)acetamide.

Workup

  1. temperatureThe solution is cooled
  2. extractionextracted with ethyl acetate
  3. washThe extract is washed with aqueous sodium carbonate and water
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-930c01df856b4a538de404b344c0c34b
Source dataset
uspto-grants-1976_09
Patent number
US03979430

Reaction notes

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