Water → HCID 20459610, compound

HRID 1283499Notes

Reaction equation

HRID 1283499 reaction equation
[C:1]([C:4]1[CH:20]=[CH:19][CH:18]=[CH:17][C:5]=1[CH2:6][CH2:7][C:8]1[CH:9]=[C:10]([CH2:14][C:15]#[N:16])[CH:11]=[CH:12][CH:13]=1)(O)=[O:2].[OH2:21]>>[O:2]=[C:1]1[C:13]2[CH:12]=[CH:11][C:10]([CH2:14][C:15]([NH2:16])=[O:21])=[CH:9][C:8]=2[CH2:7][CH2:6][C:5]2[CH:17]=[CH:18][CH:19]=[CH:20][C:4]1=2

Participants

3

Reactant 2

HCID 962WaterHCID 21518338HCID 21518338, compound

Product 1

HCID 20459610HCID 20459610, compound

Conditions

Temperature
100 °C

Procedure

3-(2-Carboxyphenethyl)phenylacetonitrile (2 g.) is added to polyphosphoric acid (20 g.) [prepared from orthophosphoric acid (d = 1.7; 1,120 g.) and phosphorus pentoxide (1,300 g.)], and the mixture is heated for 2 hours at 100°C. After cooling, the reaction mixture is poured into water (250 cc.); the oil which separates out is extracted twice with methylene chloride (total 150 cc.). The combined organic extracts are washed and dried over anhydrous sodium sulphate (10 g.) and the solvent is evaporated under reduced pressure (20 mm.Hg) at 60°C. to give (5-oxo-10,11-dihydrodibenzo[a,d]cyclohepten-2-yl)acetamide (1.8 g.) melting at 174°C. After recrystallisation from ethanol, the product melts at 185°C.

Workup

  1. temperatureAfter cooling
  2. extractionthe oil which separates out is extracted twice with methylene chloride (total 150 cc.)
  3. washThe combined organic extracts are washed
  4. dry with materialdried over anhydrous sodium sulphate (10 g.)
  5. customthe solvent is evaporated under reduced pressure (20 mm.Hg) at 60°C.

Sources & evidence

ORD record
ord-a639b4f3e1054c8f85663ea34b6566b9
Source dataset
uspto-grants-1976_08
Patent number
US03975437

Reaction notes

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