Hydroxyamine hydrochloride → HCID 86755153, compound

HRID 377647Notes

Reaction equation

HRID 377647 reaction equation
[C:1]([C:4]1[C:5]([C:22]#[N:23])=[N:6][N:7]([C:10]2[C:15]([Cl:16])=[CH:14][C:13]([C:17]([F:20])([F:19])[F:18])=[CH:12][C:11]=2[Cl:21])[C:8]=1[NH2:9])(=O)[CH3:2].Cl.[NH2:25][OH:26]>N1C=CC=CC=1>[NH2:9][C:8]1[N:7]([C:10]2[C:15]([Cl:16])=[CH:14][C:13]([C:17]([F:20])([F:19])[F:18])=[CH:12][C:11]=2[Cl:21])[N:6]=[C:5]([C:22]#[N:23])[C:4]=1[C:1](=[N:25][OH:26])[CH3:2]

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 21188137HCID 21188137, compound

Product 1

HCID 86755153HCID 86755153, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirred solution of 4-acetyl-5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole (0.25g) in pyridine (5 ml) was added hydroxylamine hydrochloride (0.05 g). After stirring at room temperature for 6 hours the mixture was heated at 50° C. for 3 hours, after which it was evaporated. The residue was taken up in ether and washed with aqueous citric acid solution (1M), water, then dried and evaporated. The residue was crystallised from propan-2-ol/hexane and further purified by column chromatography on silica gel eluted with dichloromethane. Combination and evaporation of suitable fractions gave the title compound as a tan solid, m.p. 105-110° C.

Workup

  1. temperaturewas heated at 50° C. for 3 hours
  2. customafter which it was evaporated
  3. washwashed with aqueous citric acid solution (1M), water
  4. customdried
  5. customevaporated
  6. customThe residue was crystallised from propan-2-ol/hexane
  7. customfurther purified by column chromatography on silica gel
  8. washeluted with dichloromethane
  9. customCombination and evaporation of suitable fractions

Sources & evidence

ORD record
ord-c793a9e3ecc94ea7ac7a1b790afb485a
Source dataset
uspto-grants-2000_02
Patent number
US06028096

Reaction notes

Loading…