Phosphorus oxide (P4O10) → HCID 12851824, compound

HRID 1156891Notes

Reaction equation

HRID 1156891 reaction equation
[N+:1]([C:4]1[CH:23]=[CH:22][C:7]([C:8]([NH:10][CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[CH2:19][C:20]#[N:21])=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>C1(C)C(C)=CC=CC=1.P(Cl)(Cl)(Cl)=O>[N+:1]([C:4]1[CH:23]=[CH:22][C:7]([C:8]2[C:18]3[CH:17]=[CH:16][CH:15]=[C:14]([CH2:19][C:20]#[N:21])[C:13]=3[CH2:12][CH2:11][N:10]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 2

HCID 14812Phosphorus oxide (P4O10)HCID 12851817HCID 12851817, compound

Product 1

HCID 12851824HCID 12851824, compoundYield 75.2%

Reagents, catalysts & solvents 2

HCID 7237O-XyleneSolventHCID 24813Phosphorus oxychlorideSolvent

Conditions

Temperature
140 °C

Procedure

1-(4-Nitrobenzoyl)amino-2-(2-cyanomethylphenyl)-ethane (12.7 g) was dissolved in 128 ml of xylene and 77 ml of phosphorus oxychloride. While the solution was heated with stirring over an oil bath at 140° C., 38 g of phosphorus pentoxide was added gradually. The reaction was performed for 7 hours. The upper layer of the reaction mixture was removed by decantation. Ice water was added to the residue, and an aqueous solution of sodium hydroxide was added to make it neutral. The crystals that precipitated were collected by filtration, and recrystallized from ethanol to afford 9 g of 1-(4-nitrophenyl)-3,4-dihydroisoquinoline-5-acetonitrile having a melting point of 137.7° to 138.7° C.

Workup

  1. temperatureWhile the solution was heated
  2. customThe upper layer of the reaction mixture was removed by decantation
  3. additionIce water was added to the residue
  4. additionan aqueous solution of sodium hydroxide was added
  5. customThe crystals that precipitated
  6. filtrationwere collected by filtration
  7. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-3d5f35c9029d41a0ac8388a71cf76737
Source dataset
uspto-grants-1982_06
Patent number
US04337256

Reaction notes

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