Acetone → Ethyl 4-hydroxy-7-nitro-2-oxo-1,2-dihydro-quinoline-3-carboxylate

HRID 2294204Notes

Reaction equation

HRID 2294204 reaction equation
C(N(CC)CC)C.Cl.[NH2:9][C:10]1[CH:20]=[C:19]([N+:21]([O-:23])=[O:22])[CH:18]=[CH:17][C:11]=1[C:12]([O:14]CC)=O.C[CH:25]([C:29](Cl)=[O:30])[C:26](Cl)=[O:27].[Na].C[C:34]([CH3:36])=[O:35]>C(O)C>[OH:14][C:12]1[C:11]2[C:10](=[CH:20][C:19]([N+:21]([O-:23])=[O:22])=[CH:18][CH:17]=2)[NH:9][C:26](=[O:27])[C:25]=1[C:29]([O:35][CH2:34][CH3:36])=[O:30]

Participants

7

Reactant 5

HCID 180AcetoneHCID 8471TriethylamineHCID 5360545SodiumHCID 10931669MethylmalonylchlorideHCID 21473954Ethyl 2-amino-4-nitrobenzoate hydrochloride

Product 1

HCID 54681153Ethyl 4-hydroxy-7-nitro-2-oxo-1,2-dihydro-quinoline-3-carboxylateYield 60%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

7.7 ml of triethylamine (55 mmol) were added dropwise to a suspension of 10.0 g of ethyl 2-amino-4-nitrobenzoate hydrochloride (4.3 mmol) in 100 ml of acetone. Subsequently, 6.55 ml of methylmalonyl chloride (52 mmol) were added. The reaction mixture was left to stir at room temperature for 48 hrs., concentrated and then treated with a solution of 4.2 g of sodium (183 mmol) in 110 ml of ethanol. The reaction mixture was boiled at reflux for 2.5 hrs. After removing the solvent the residue was taken up in 200 ml of water and heated to 60° C. for 1 hr. Subsequently, the mixture was filtered over Dicalite and thereafter the pH value was adjusted to pH=3.5 with 3N HCl. The precipitate which thereby separated was filtered off, washed with water and dried in a high vacuum. There were obtained 7.2 g of ethyl 4-hydroxy-7-nitro-2-oxo-1,2-dihydro-quinoline-3-carboxylate (60%) as beige crystals.

Workup

  1. waitThe reaction mixture was left
  2. concentration, concentrated
  3. temperatureat reflux for 2.5 hrs
  4. customAfter removing the solvent the residue
  5. temperatureheated to 60° C. for 1 hr
  6. filtrationSubsequently, the mixture was filtered over Dicalite
  7. customThe precipitate which thereby separated
  8. filtrationwas filtered off
  9. washwashed with water
  10. customdried in a high vacuum

Sources & evidence

ORD record
ord-5106692112ab40a3ba63ca49d3b4a575
Source dataset
uspto-grants-1997_11
Patent number
US05688803

Reaction notes

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