Methyl 3-amino-4-methylbenzoate → methyl 1H-indazole-6-carboxylate

HRID 1780923Notes

Reaction equation

HRID 1780923 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[C:6]([NH2:11])[CH:5]=1.[N:13]([O-])=O.[Na+]>C(O)(=O)C.O>[NH:11]1[C:6]2[C:7](=[CH:8][CH:9]=[C:4]([C:3]([O:2][CH3:1])=[O:12])[CH:5]=2)[CH:10]=[N:13]1

Participants

5

Reactant 2

HCID 337778Methyl 3-amino-4-methylbenzoateHCID 23668193Sodium Nitrite

Product 1

HCID 286535methyl 1H-indazole-6-carboxylateYield 71.9%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To a solution of 3-amino-4-methylbenzoic acid methyl ester (25 g, 0.15 mol) in 1 L of acetic acid cooled to 0° C. was added a solution of NaNO2 (12.5 g, 0.182 mol) in 50 ml of water and the mixture was warmed to room temperature with stirring over 4 hours. The solution was concentrated in vacuo, the residue was triturated with water, the solid was filtered and washed with water and hexane to afford 19 g (71.6%) of methyl indazole-6-carboxylate.

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. customthe residue was triturated with water
  3. filtrationthe solid was filtered
  4. washwashed with water and hexane

Sources & evidence

ORD record
ord-fee2b76fa72f4ff9b4a4d85aa6743379
Source dataset
uspto-grants-1997_05
Patent number
US05631264

Reaction notes

Loading…