HCID 54076451, compound → HCID 20462462, compound

HRID 326096Notes

Reaction equation

HRID 326096 reaction equation
[C:1]([NH:9][CH2:10][CH2:11][C:12]1[NH:13][C:14]2[C:19]([C:20]=1[CH2:21][C:22]([NH2:24])=O)=[CH:18][CH:17]=[CH:16][CH:15]=2)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>P(Cl)(Cl)(Cl)=O>[C:2]1([C:1]2[N:13]3[C:14]4[C:19]([C:20]([CH2:21][C:22]#[N:24])=[C:12]3[CH2:11][CH2:10][N:9]=2)=[CH:18][CH:17]=[CH:16][CH:15]=4)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 54076451HCID 54076451, compound

Product 1

HCID 20462462HCID 20462462, compound

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

1.6 g (0.005 mol) of 2-(benzoylamino-ethyl)-indole-3-acetamide is heated under reflux for 2 hours in 16 ml of phosphorus oxychloride. Excess phosphorus oxychloride is distilled off, the oily residue is taken up in water and by-products of the reaction are removed by extracting with ether. Concentrated ammonia is added to the aqueous phase, while cooling, and extraction with ether is carried out. After washing and drying the ether phase and concentrating it by evaporation, 1-phenyl-3,4-dihydro-pyrimido[1,6-a]indole-5-acetonitrile is obtained as a yellowish oil which, by dissolving in methanol and adding ethereal hydrochloric acid, can be converted into a crystalline hydrochloride having a melting point of 195°-205°.

Workup

  1. distillationExcess phosphorus oxychloride is distilled off
  2. customby-products of the reaction are removed
  3. extractionby extracting with ether
  4. additionConcentrated ammonia is added to the aqueous phase
  5. temperaturewhile cooling
  6. extractionextraction with ether
  7. washAfter washing
  8. dry with materialdrying the ether phase
  9. concentrationconcentrating it
  10. customby evaporation

Sources & evidence

ORD record
ord-81a58f81a32f404bab53d350b047b3bc
Source dataset
uspto-grants-1984_04
Patent number
US04444768

Reaction notes

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