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

HRID 530214Notes

Reaction equation

HRID 530214 reaction equation
O[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:15]#[N:16].O=P(Cl)(Cl)[Cl:19]>>[Cl:19][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:15]#[N:16]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178510310HCID 178510310, compound

Product 1

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

Conditions

Temperature
0 °C

Procedure

mixture of 4-hydroxy-6-nitroquinoline-3-carbonitrile (11.0 g) and 50 mL of POCl3 was heated at reflux for 7 hours. The volatile materials were removed under vacuum at 70° C. The residue was stirred at 0° C. with methylene chloride and H2O, and solid K2CO3 was carefully added until the pH was 8-9. After stirring for 30 min at rt, the organic layer was separated, washed with H2O, dried and evaporated under vacuum to give a crude solid. Purification on a silica gel column gave the 4-chloro-6-nitroquinoline-3-carbonitrile (Compound 17) as an off-white solid (4.2 g).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 7 hours
  3. customThe volatile materials were removed under vacuum at 70° C
  4. additionwas carefully added until the pH was 8-9
  5. stirringAfter stirring for 30 min at rt
  6. customthe organic layer was separated
  7. washwashed with H2O
  8. customdried
  9. customevaporated under vacuum
  10. customto give a crude solid
  11. customPurification on a silica gel column

Sources & evidence

ORD record
ord-b07b95e12cf04c3c87c84ed8f10a9ef9
Source dataset
uspto-grants-2016_05
Patent number
US09353062B2

Reaction notes

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