Water → 1-(2-Carboxy-3-methoxyphenyl)-3-methyl-6-nitroindazole

HRID 1588064Notes

Reaction equation

HRID 1588064 reaction equation
[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([N+:11]([O-:13])=[O:12])=[CH:8][CH:9]=2)[NH:4][N:3]=1.Br[C:15]1[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH3:25])[C:16]=1[C:17]([OH:19])=[O:18].C(=O)([O-])[O-].[K+].[K+].O>[N+](C1C=CC=CC=1)([O-])=O.[Cu]=O>[C:17]([C:16]1[C:20]([O:24][CH3:25])=[CH:21][CH:22]=[CH:23][C:15]=1[N:4]1[C:5]2[C:10](=[CH:9][CH:8]=[C:7]([N+:11]([O-:13])=[O:12])[CH:6]=2)[C:2]([CH3:1])=[N:3]1)([OH:19])=[O:18]

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 109210543-Methyl-6-nitro-1H-indazoleHCID 111178812-Bromo-6-methoxybenzoic acid

Product 1

HCID 110347721-(2-Carboxy-3-methoxyphenyl)-3-methyl-6-nitroindazoleYield 75.9%

Reagents, catalysts & solvents 2

HCID 14829Copper oxideCatalystHCID 7416NitrobenzeneSolvent

Procedure

3-Methyl-6-nitroindazole (5.31 g), 6.93 g of 2-bromo-6-methoxybenzoic acid, 4.71 g of potassium carbonate and 0.218 g of copper (II) oxide were stirred in 60 ml of nitrobenzene at 180° C. for 50 minutes. After cooling, 300 ml of water was added to the reaction mixture, and the insoluble substance was removed by filtration. The resulting solution was washed with chloroform. The aqueous layer was decolored with active charcoal and filtered, and 40 ml of 1 N hydrochloric acid aqueous solution was added to the filtrate. The crystals precipitated were separated by filtration and dried under reduced pressure to obtain 7.45 g (75.9%) of 1-(2-carboxy-3-methoxyphenyl)-3-methyl-6-nitroindazole.

Workup

  1. temperatureAfter cooling
  2. customthe insoluble substance was removed by filtration
  3. washThe resulting solution was washed with chloroform
  4. filtrationfiltered
  5. addition40 ml of 1 N hydrochloric acid aqueous solution was added to the filtrate
  6. customThe crystals precipitated
  7. customwere separated by filtration
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-87e0d46a6e154a4c93b81866d7586780
Source dataset
uspto-grants-1993_06
Patent number
US05220026

Reaction notes

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