Phosphorus oxide (P4O10) → 7-chloro-2,3-dihydro-8-nitro-4(1H)-quinolinone

HRID 1886444Notes

Reaction equation

HRID 1886444 reaction equation
[Cl:1][C:2]1[C:3]([N+:14]([O-:16])=[O:15])=[C:4]([NH:8][CH2:9][CH2:10][C:11]([OH:13])=O)[CH:5]=[CH:6][CH:7]=1.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:3]([N+:14]([O-:16])=[O:15])=[C:4]2[C:5]([C:11](=[O:13])[CH2:10][CH2:9][NH:8]2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14812Phosphorus oxide (P4O10)HCID 198759993-(3-Chloro-2-nitrophenylamino)propionic acid

Product 1

HCID 107279787-chloro-2,3-dihydro-8-nitro-4(1H)-quinolinoneYield 50.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 3-(3-chloro-2-nitrophenylamino)propionic acid (21.5 g), which was synthesized according to the method of Giovanni Pappalardo et al. (Ann. Chim. (Rome), 55, 182 (1965)), phosphorus pentoxide (37.0 g) and toluene (160 ml) was refluxed for 90 minutes. After cooling, toluene was removed in vacuo. The residue was washed with ether to give 7-chloro-2,3-dihydro-8-nitro-4(1H)-quinolinone (yield 10.0 g).

Workup

  1. customwas synthesized
  2. temperaturewas refluxed for 90 minutes
  3. temperatureAfter cooling
  4. customtoluene was removed in vacuo
  5. washThe residue was washed with ether

Sources & evidence

ORD record
ord-15139132bc374eb2bf43cb9f37aff75e
Source dataset
uspto-grants-1992_09
Patent number
US05151431

Reaction notes

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