Water → HCID 12851825, compound

HRID 1156898Notes

Reaction equation

HRID 1156898 reaction equation
[C:1]1([CH3:19])[CH:6]=[CH:5][C:4]([C:7]([NH:9][CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[Cl:18])=O)=[CH:3][CH:2]=1.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.O.[OH-].[Na+]>C1(C)C(C)=CC=CC=1.P(Cl)(Cl)(Cl)=O>[CH3:19][C:1]1[CH:6]=[CH:5][C:4]([C:7]2[C:17]3[C:12](=[C:13]([Cl:18])[CH:14]=[CH:15][CH:16]=3)[CH2:11][CH2:10][N:9]=2)=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 14812Phosphorus oxide (P4O10)HCID 128518181-(p-Toluoylamino)-2-(2-chlorophenyl)ethane

Product 1

HCID 12851825HCID 12851825, compoundYield 44.3%

Reagents, catalysts & solvents 2

HCID 7237O-XyleneSolventHCID 24813Phosphorus oxychlorideSolvent

Procedure

1-(p-Toluoylamino)-2-(2-chlorophenyl)ethane (70 g) was dissolved in 700 ml of xylene and 320 ml of phosphorus oxychloride, and while the solution was heated with stirring, 240 g of phosphorus pentoxide was added. The mixture was heated under reflux for 4 hours. Water was added to the reaction mixture. The aqueous layer was made weakly alkaline with an aqueous solution of sodium hydroxide, extracted with benzene, washed in water, and dried. The solvent was distilled off, and the residue was recrystallized from benzene to afford 29 g of 1-(4-methylphenyl)-5-chloro-3,4-dihydroisoquinoline as colorless needles.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 4 hours
  3. extractionextracted with benzene
  4. washwashed in water
  5. customdried
  6. distillationThe solvent was distilled off
  7. customthe residue was recrystallized from benzene

Sources & evidence

ORD record
ord-7719e64ba9a14481bd262f072a3001eb
Source dataset
uspto-grants-1982_06
Patent number
US04337256

Reaction notes

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