Hydrochloric Acid → 1-Hydroxybenzotriazole

HRID 734174Notes

Reaction equation

HRID 734174 reaction equation
Cl[C:2]1[CH:10]=[CH:9][C:5](C(O)=O)=[CH:4][C:3]=1[N+:11]([O-:13])=O.O.[NH2:15][NH2:16].Cl>C(O)C.O>[OH:13][N:11]1[C:3]2[CH:4]=[CH:5][CH:9]=[CH:10][C:2]=2[N:16]=[N:15]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 73204-Chloro-3-nitrobenzoic acidHCID 24654Hydrazine hydrate (1:1)

Product 1

HCID 757711-Hydroxybenzotriazole

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Referring to FIG. 1, 1-hydroxybenzotriazole-6-carboxylic acid is formed in two steps from 4-chloro-3-nitrobenzoic acid. In the first step, 4-chloro-3-nitrobenzoic acid and hydrazine monohydrate are heated at reflux in ethanol to yield a crude precipitate. In the second step, the crude precipitate is dissolved in water and acidified with HCl to pH 1 to yield 1-hydroxybenzotriazole, a peach colored precipitate. Confirmation of the compound can be conducted by NMR spectroscopy and high resolution mass spectroscopy (HRMS), as well as other detection methods determined by one of skill in the art.

Workup

  1. customto yield a crude precipitate

Sources & evidence

ORD record
ord-8256435b4fc4460e97819ccaf52cb5bb
Source dataset
uspto-grants-2009_09
Patent number
US07592183B2

Reaction notes

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