Phosphorus oxychloride → 4-Chloro-6-nitroquinoline-3-carbonitrile

HRID 548410Notes

Reaction equation

HRID 548410 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[NH:10][CH:9]=[C:8]([C:14]#[N:15])[C:7]2=O)([O-:3])=[O:2].P(Cl)(Cl)([Cl:19])=O>>[Cl:19][C:7]1[C:6]2[C:11](=[CH:12][CH:13]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[N:10]=[CH:9][C:8]=1[C:14]#[N:15]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 110530426-Nitro-4-oxo-1,4-dihydroquinoline-3-carbonitrile

Product 1

HCID 110856904-Chloro-6-nitroquinoline-3-carbonitrile

Procedure

A mixture of 31.3 g (0.147 mol) of 6-nitro-4-oxo-1,4-dihydro-quinoline-3-carbonitrile and 160 mL of phosphorous oxychloride was refluxed for 5.5 h. The phosphorous oxychloride was removed in vacuo and the residue was poured over ice and neutralized with sodium bicarbonate. The product was collected, washed with water and dried in vacuo (50° C.). There was obtained 33.5 g of tan solid; solid: mass spectrum (electrospray, m/e): M+H 234.

Workup

  1. temperaturewas refluxed for 5.5 h
  2. customThe phosphorous oxychloride was removed in vacuo
  3. additionthe residue was poured over ice and neutralized with sodium bicarbonate
  4. customThe product was collected
  5. washwashed with water
  6. customdried in vacuo (50° C.)

Sources & evidence

ORD record
ord-7307bb2e73254f93838c485c4b299a6b
Source dataset
uspto-grants-2011_05
Patent number
USRE042376E1

Reaction notes

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