Hydrochloric Acid → Methyl 5-nitro-1H-indazole-3-carboxylate

HRID 1038128Notes

Reaction equation

HRID 1038128 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][N:8]=[C:7]2[C:13]([OH:15])=[O:14])([O-:3])=[O:2].O=S(Cl)Cl.Cl.[CH3:21]O>>[CH3:21][O:14][C:13]([C:7]1[C:6]2[C:10](=[CH:11][CH:12]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[NH:9][N:8]=1)=[O:15]

Participants

5

Reactant 4

HCID 313Hydrochloric Acid2×HCID 887MethanolHCID 24386Thionyl ChlorideHCID 71446525-nitro-1H-indazole-3-carboxylic Acid

Product 1

HCID 12689299Methyl 5-nitro-1H-indazole-3-carboxylate

Conditions

Temperature
0 °C

Procedure

To a suspension of 5-nitro-1H-indazole-3-carboxylic acid 17AP (10.74 g, 51.88 mmol) in MeOH (145 ml) at 0° C. was added SOCl2 (35 ml) dropwise. After stirring for 10 min at 0° C., the reaction mixture was refluxed overnight. HCl gas was evolved (Condenser was equipped with empty balloon to trap HCl). It was then cooled to room temperature, solid was collected by filtration and washed with MeOH to give desired 5-nitro-1H-indazole-3-carboxylic acid methyl ester 18AP (7 g, 61%).

Workup

  1. temperaturethe reaction mixture was refluxed overnight
  2. temperatureIt was then cooled to room temperature
  3. filtrationsolid was collected by filtration
  4. washwashed with MeOH

Sources & evidence

ORD record
ord-75b93eded7b94df880231c47dd19dd41
Source dataset
uspto-grants-2013_10
Patent number
US08546404B2

Reaction notes

Loading…