Acetic Acid → HCID 20060977, compound

HRID 1085228Notes

Reaction equation

HRID 1085228 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2C=1N[C:11](=[O:14])[C:10]2=[O:15])=O.[N+:16](=[CH2:18])=[N-].[C:19]([OH:22])(=[O:21])C>CCOCC>[OH:15][C:10]1[C:11](=[O:14])[N:16]([C:19]([OH:22])=[O:21])[C:18]2[C:8]([CH:9]=1)=[CH:7][CH:6]=[CH:5][C:3]=2[O:2][CH3:1]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 9550DiazomethaneHCID 1946733Methyl 2,3-dioxo-2,3-dihydro-1H-indole-7-carboxylate

Product 1

HCID 20060977HCID 20060977, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A suspension of 7-methoxycarbonylisatin (2.4 g) in ether (50 ml) was treated at 31 5° C. with a solution of diazomethane (1.5 g) in ether (140 ml). The mixture was stirred for 3 hours and acetic acid (3 ml) added. The mixture was filtered and the filtrate concentrated under reduced pressure to give a residue that was purified by column chromatograph (silica gel eluting with dichloromethane/methanol) to give 3-hydroxy-8-methoxycarboxy-2-(1H)-quinolinone (350 mg). This in methanol (10 ml) was treated with 2N sodium hydroxide (1.75 ml) at room temperature for 2.5 hours. The mixture was acidified with 2N HCl and the precipitate was collected and dried to give 3-hydroxy-8-carboxy-2(1H)-quinolinone (180 mg); NMR (DMSO-d6 /CF3COOD) 7.12-7.30(m,2H); 7.75(d,1H); 8.01(d,1H).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate concentrated under reduced pressure
  3. customto give a residue that
  4. customwas purified by column chromatograph (silica gel eluting with dichloromethane/methanol)

Sources & evidence

ORD record
ord-614f2c59f17046bd9d74b2e252555d95
Source dataset
uspto-grants-1991_04
Patent number
US05008259

Reaction notes

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