Hydrochloric Acid → 1-hydroxy-alpha-phenyl-1H-benzotriazole-6-methanol

HRID 2248322Notes

Reaction equation

HRID 2248322 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[OH:9])=[CH:4][C:3]=1[N+:16]([O-:18])=O.O.[NH2:20][NH2:21].Cl>C(O)C>[OH:18][N:16]1[C:3]2[CH:4]=[C:5]([CH:8]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[OH:9])[CH:6]=[CH:7][C:2]=2[N:21]=[N:20]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24654Hydrazine hydrate (1:1)HCID 14990620HCID 14990620, compound

Product 1

HCID 149906211-hydroxy-alpha-phenyl-1H-benzotriazole-6-methanolYield 98.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 25 parts of 4-fluoro-3-nitro-α-phenylbenzenemethanol, 20 parts of hydrazine monohydrate and 80 parts of ethanol was stirred for 1.5 hours at reflux temperature. After cooling, 20 parts of a hydrochloric acid solution 10N were added. After concentration, the residue was washed twice with 50 parts of water and dissolved in a solution of 300 parts methanol (10%) in trichloromethane. The organic layer was dried, filtered and concentrated, yielding 23.8 parts (98.6%) of 1-hydroxy-α-phenyl-1H-benzotriazole-6-methanol as a residue (int. 64).

Workup

  1. temperatureat reflux temperature
  2. temperatureAfter cooling
  3. concentrationAfter concentration
  4. washthe residue was washed twice with 50 parts of water
  5. dissolutiondissolved in a solution of 300 parts methanol (10%) in trichloromethane
  6. customThe organic layer was dried
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-68fe23606f374c8fad77372cd3f1001e
Source dataset
uspto-grants-1991_08
Patent number
US05039677

Reaction notes

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