Acetic Acid → methyl 1H-indazole-6-carboxylate

HRID 1360838Notes

Reaction equation

HRID 1360838 reaction equation
[N:1]([O-])=O.[Na+].[NH2:5][C:6]1[CH:7]=[C:8]([CH:13]=[CH:14][C:15]=1[CH3:16])[C:9]([O:11][CH3:12])=[O:10].C(O)(=O)C>O>[NH:5]1[C:6]2[C:15](=[CH:14][CH:13]=[C:8]([C:9]([O:11][CH3:12])=[O:10])[CH:7]=2)[CH:16]=[N:1]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 337778Methyl 3-amino-4-methylbenzoateHCID 23668193Sodium Nitrite

Product 1

HCID 286535methyl 1H-indazole-6-carboxylateYield 80.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

2.47 g (34.5 mmol) of sodium nitrite was dissolved in 3.8 ml of water, and it was added dropwise to a mixture of 5.64 g (34.1 mmol) of methyl 3-amino-4-methyl-benzoate and 140 ml of acetic acid under ice-cooling. After the temperature of the reaction mixture was allowed to warm to room temperature and the mixture was stirred overnight, water was added to the mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, and then dried over magnesium sulfate and filtered. The solvent was distilled off to give 4.83 g (yield: 80%) of methyl indazole-6-carboxylate.

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-08f894df80ff49ad93262611c3776703
Source dataset
uspto-grants-2011_02
Patent number
US07879887B2

Reaction notes

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