Formaldehyde → 1-Hydroxymethyl-3-phenylindazole

HRID 1730940Notes

Reaction equation

HRID 1730940 reaction equation
[C:1]1([C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[NH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:16]=[O:17].[OH-].[Na+]>C(O)C>[OH:17][CH2:16][N:9]1[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[N:8]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 3003853-phenyl-1H-indazole

Product 1

HCID 132925841-Hydroxymethyl-3-phenylindazoleYield 77.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-Phenylindazole (9.71 g), paraformaldehyde (2.25 g) and 5% aqueous sodium hydroxide solution (1 ml) were added to ethanol (40 ml) and the mixture was heated under reflux for 3 hours. After cooling the reaction mixture, the precipitated crystals were recovered by filtration to obtain 8.7 g of 1-hydroxymethyl-3-phenylindazole having a melting point between 103°-105° C after recrystallization from ligroine.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 3 hours
  3. temperatureAfter cooling the reaction mixture
  4. filtrationthe precipitated crystals were recovered by filtration

Sources & evidence

ORD record
ord-969ed7aa68484e108babc158379aa2fe
Source dataset
uspto-grants-1976_11
Patent number
US03994890

Reaction notes

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