Acetic Acid → HCID 178418469, compound

HRID 3133

Reaction equation

HRID 3133 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([N+:12]([O-])=O)[CH:10]=2)[N:5]=[C:4]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:3]=1[C:20]([O:22][CH2:23][CH3:24])=[O:21].C(O)(=O)C>C(O)C.[Fe]>[NH2:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[N:5]=[C:4]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:3]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[C:2]2[OH:1]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 178418399HCID 178418399, compound

Product 1

HCID 178418469HCID 178418469, compoundYield 75.3%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

A stirred mixture of diethyl 4-hydroxy-6-nitroquinoline-2,3-dicarboxylate (4.4 g, 13 mM), powdered iron (6.6 g, 118 mM) and glacial acetic acid (18.5 g, 307 mM) in ethanol (80 mL) was refluxed for 20 hr under a nitrogen atmosphere. The reaction mixture was cooled and filtered and the filtrate was concentrated. The dark residue was chromatographed (eluant: methylene chloride/methanol; 98/2) over silical gel to provide (3.01 g, 75.3%) the title compound as light orange crystals, mp 219°-221° C.; MS(CI): 305 (M+H).

Workup

  1. temperaturewas refluxed for 20 hr under a nitrogen atmosphere
  2. temperatureThe reaction mixture was cooled
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated
  5. customThe dark residue was chromatographed (eluant: methylene chloride/methanol; 98/2) over silical gel

Sources & evidence

ORD record
ord-d22c33b8f7f941c2ae9d370668c316af
Source dataset
uspto-grants-1998_03
Patent number
US05733910

Linked notes

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