Phosphorus oxychloride → 2-Amino-3-cyano-4-chloro-6-nitroquinoline

HRID 1985697Notes

Reaction equation

HRID 1985697 reaction equation
[NH2:1][C:2]1[C:11]([C:12]#[N:13])=[C:10](O)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([N+:15]([O-:17])=[O:16])[CH:8]=2)[N:3]=1.P(Cl)(Cl)([Cl:20])=O>>[NH2:1][C:2]1[C:11]([C:12]#[N:13])=[C:10]([Cl:20])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([N+:15]([O-:17])=[O:16])[CH:8]=2)[N:3]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178510460HCID 178510460, compound

Product 1

HCID 668506012-Amino-3-cyano-4-chloro-6-nitroquinoline

Procedure

The stirred mixture of 48.5 g of 2-amino-3-cyano-4-hydroxy-6-nitroquinoline and 550 mL of phosphoryl chloride was refluxed for 4 hours. The reaction mixture was concentrated to half of its volume and the residue was poured onto 1500 g of ice. The yellow precipitate was filtered off, washed with water to give 60.5 g of solid. 25 g of this solid was stirred at room temperature in 500 mL of 0.5 N HCl for 6 hours, then the precipitate was filtered off, washed with water to give 18.5 g of product, m.p.: >360° C. LC-MS: MH+ 249; Ret. time: 5.94 min.

Workup

  1. temperaturewas refluxed for 4 hours
  2. concentrationThe reaction mixture was concentrated to half of its volume
  3. additionthe residue was poured onto 1500 g of ice
  4. filtrationThe yellow precipitate was filtered off
  5. washwashed with water

Sources & evidence

ORD record
ord-b9f902588a734a72970bbc81070b4043
Source dataset
uspto-grants-2009_06
Patent number
US07547696B2

Reaction notes

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