Phosphorus oxide (P4O10) → 1-(4-Chlorophenyl)-5-methyl-3,4-dihydroisoquinoline

HRID 1156862Notes

Reaction equation

HRID 1156862 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][C:5]([C:6]([NH:8][CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[CH3:17])=O)=[CH:4][CH:3]=1.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>C1(C)C(C)=CC=CC=1.P(Cl)(Cl)(Cl)=O>[Cl:1][C:2]1[CH:19]=[CH:18][C:5]([C:6]2[C:16]3[C:11](=[C:12]([CH3:17])[CH:13]=[CH:14][CH:15]=3)[CH2:10][CH2:9][N:8]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 14812Phosphorus oxide (P4O10)HCID 128518081-(4-Chlorobenzoylamino)-2-(2-methylphenyl)ethane

Product 1

HCID 128518201-(4-Chlorophenyl)-5-methyl-3,4-dihydroisoquinoline

Reagents, catalysts & solvents 2

HCID 7237O-XyleneSolventHCID 24813Phosphorus oxychlorideSolvent

Procedure

Thirty-six (36) grams of 1-(4-chlorobenzoylamino)-2-(2-methylphenyl)ethane was dissolved in 180 ml of xylene and 100 ml of phosphorus oxychloride. While the solution was heated with stirring, 80 g of phosphorus pentoxide was added gradually, and the mixture was heated under reflux. The reaction mixture was poured into ice water. The aqueous layer was separated, and made weakly alkaline with ammonia water. Recrystallization of the precipitated oily product from n-hexane afforded 31 g of 1-(4-chlorophenyl)-5-methyl-3,4-dihydroisoquinoline as colorless prisms having a melting point of 66° to 67° C.

Workup

  1. temperatureWhile the solution was heated
  2. temperaturethe mixture was heated
  3. temperatureunder reflux
  4. customThe aqueous layer was separated
  5. customRecrystallization of the precipitated oily product from n-hexane

Sources & evidence

ORD record
ord-eb698f39bfea4d6bba3372fef029985d
Source dataset
uspto-grants-1982_06
Patent number
US04337256

Reaction notes

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