Water → HCID 21518347, compound

HRID 1283497Notes

Reaction equation

HRID 1283497 reaction equation
[C:1]([C:4]1[CH:21]=[CH:20][CH:19]=[CH:18][C:5]=1[CH2:6][CH2:7][C:8]1[CH:9]=[C:10]([CH:14]([CH3:17])[C:15]#[N:16])[CH:11]=[CH:12][CH:13]=1)([OH:3])=O.[OH2:22]>C(Cl)Cl.C(OCC)(=O)C>[O:3]=[C:1]1[C:13]2[CH:12]=[CH:11][C:10]([CH:14]([CH3:17])[C:15]([NH2:16])=[O:22])=[CH:9][C:8]=2[CH2:7][CH2:6][C:5]2[CH:18]=[CH:19][CH:20]=[CH:21][C:4]1=2

Participants

5

Reactant 2

HCID 962WaterHCID 21518335HCID 21518335, compound

Product 1

HCID 21518347HCID 21518347, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

2-[3-(2-Carboxyphenethyl)phenyl]propionitrile (26 g.) is added to polyphosphoric acid (135 g.) [prepared from orthophosphoric acid (d = 1.7; 430 g.) and phosphorus pentoxide (500 g.)] and the emulsion obtained is heated for 1 hour at 100°C. After cooling, the reaction mixture is taken up in water (200 cc.) and methylene chloride (200 cc.). The organic layer is decanted, washed with a saturated solution of sodium bicarbonate (2 × 100 cc.) and then with water (2 × 100 cc.) and is finally dried over anhydrous sodium sulphate (50 g.). After evaporation of the solvent under reduced pressure (20 mm.Hg) at 60°C., the oil obtained is taken up in ethyl acetate (80 cc.). The product which crystallises is filtered off to give 2-(5-oxo-10,11-dihydrodibenzo[a,d]cyclohepten-2-yl)propionamide (6 g.), melting at 175°C. After recrystallisation from ethanol, the product melts at 181°C.

Workup

  1. customthe emulsion obtained
  2. temperatureAfter cooling
  3. customThe organic layer is decanted
  4. washwashed with a saturated solution of sodium bicarbonate (2 × 100 cc.)
  5. dry with materialwith water (2 × 100 cc.) and is finally dried over anhydrous sodium sulphate (50 g.)
  6. customAfter evaporation of the solvent under reduced pressure (20 mm.Hg) at 60°C.
  7. customthe oil obtained
  8. customThe product which crystallises
  9. filtrationis filtered off

Sources & evidence

ORD record
ord-ef67fde000ab446a9299b2e2ca40ac1f
Source dataset
uspto-grants-1976_08
Patent number
US03975437

Reaction notes

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