Hydrochloric Acid → Ethyl 1H-indazole-5-carboxylate

HRID 1498899Notes

Reaction equation

HRID 1498899 reaction equation
C([N:4]1[C:12]2[C:7](=[CH:8][C:9]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:10][CH:11]=2)[CH:6]=[N:5]1)(=O)C.Cl.O.O.N>C(O)C>[NH:4]1[C:12]2[C:7](=[CH:8][C:9]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:10][CH:11]=2)[CH:6]=[N:5]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 1519478Ethyl 1-acetyl-1H-indazole-5-carboxylateHCID 12896473Azane;hydrate

Product 1

HCID 1501980Ethyl 1H-indazole-5-carboxylateYield 48%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The resulting ethyl 1-acetyl-1H-indazole-5-carboxylate was stirred in a mixture of concentrated hydrochloric acid (15 ml), water (15 ml) and ethanol (30 ml) for 15 hours at a room temperature. The resulting mixture was rendered faintly alkaline with a 25% ammonia water. The faintly alkalified mixture was subjected to extraction with chloroform. The extract was crystallized from n-hexane, and then the resulting crystal was separated by filtration and dried to give the title compound (6.45 g, 48%) as a light-brown powder.

Workup

  1. extractionThe faintly alkalified mixture was subjected to extraction with chloroform
  2. customThe extract was crystallized from n-hexane
  3. customthe resulting crystal was separated by filtration
  4. customdried

Sources & evidence

ORD record
ord-4c8f5c44792c49e2b6b3696d93df8d9a
Source dataset
uspto-grants-2015_12
Patent number
US09200008B2

Reaction notes

Loading…