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

HRID 611980Notes

Reaction equation

HRID 611980 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-3-quinolinecarbonitrile 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-402bc1f83699463cb168c6342c6f90be
Source dataset
uspto-grants-1999_12
Patent number
US06002008

Reaction notes

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