Ammonia → Ethyl 4-chloro-8-nitroquinoline-3-carboxylate

HRID 1416940Notes

Reaction equation

HRID 1416940 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[C:15](=O)[C:14]2[C:9](=[C:10]([N+:17]([O-:19])=[O:18])[CH:11]=[CH:12][CH:13]=2)[N:8]=[CH:7]1)=[O:5])[CH3:2].P(Cl)(Cl)([Cl:22])=O.N>C(Cl)(Cl)Cl>[Cl:22][C:15]1[C:14]2[C:9](=[C:10]([N+:17]([O-:19])=[O:18])[CH:11]=[CH:12][CH:13]=2)[N:8]=[CH:7][C:6]=1[C:4]([O:3][CH2:1][CH3:2])=[O:5]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 24813Phosphorus oxychlorideHCID 21250014Ethyl 8-nitro-4-oxo-3,4-dihydroquinoline-3-carboxylate

Product 1

HCID 11196760Ethyl 4-chloro-8-nitroquinoline-3-carboxylateYield 75%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 3-ethoxycarbonyl-8-nitro-4-oxo-3,4-dihydro-quinoline (10.2 g) and phosphorous oxychloride (10 ml) was stirred at reflux for 2 hours. The warm reaction mixture was added cautiously to a vigorously stirred mixture of ice, concentrated aqueous ammonia and chloroform. The organic layer was separated, washed with water, dried and evaporated to dryness. The residue was purified by flash chromatography on silica using chloroform as eluant to give 4-chloro-3-ethoxycarbonyl-8-nitro-quinoline in 75% yield, mp 253-254° C.

Workup

  1. temperatureat reflux for 2 hours
  2. customThe warm reaction mixture
  3. customThe organic layer was separated
  4. washwashed with water
  5. customdried
  6. customevaporated to dryness
  7. customThe residue was purified by flash chromatography on silica

Sources & evidence

ORD record
ord-b15bec7ee9da491baa30ff78165215fb
Source dataset
uspto-grants-1999_06
Patent number
US05916898

Reaction notes

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