Hydrochloric Acid → HCID 17978859, compound

HRID 459668Notes

Reaction equation

HRID 459668 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=2)[N:5]=[CH:4][CH:3]=1.[ClH:15].[N:16](OCCC(C)C)=[O:17]>O1CCCC1>[ClH:15].[NH2:1][C:2]1[N:6]([C:7]2[CH:8]=[CH:9][C:10]([O:13][CH3:14])=[CH:11][CH:12]=2)[N:5]=[CH:4][C:3]=1[N:16]=[O:17]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8053Isoamyl NitriteHCID 218128291-(4-Methoxyphenyl)-1H-pyrazol-5-amine

Product 1

HCID 17978859HCID 17978859, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

17.4 g (92 mmol) of 5-amino-1-(4-methoxyphenyl)pyrazole [sic] from Step 1.1 was dissolved in 200 mL of tetrahydrofuran, 52.4 g of 32% hydrochloric acid was added, and the mixture was cooled to 0–5° C. Then 11.8 g (101 mmol) of isopentyl nitrite was added dropwise with agitation so that the temperature did not exceed 5° C. Gradually, a brownish precipitate formed which after an additional 2-hour agitation period in an ice bath was removed by suction filtration and washed with a small amount of tetrahydrofuran. Drying gave 16.4 g (64 mmol, 70% of the theoretical) of 5-amino-1-(4-methoxyphenyl)-4-nitrosopyrazole hydrochloride.

Workup

  1. temperaturethe mixture was cooled to 0–5° C
  2. customdid not exceed 5° C
  3. customGradually, a brownish precipitate formed which after an additional 2-hour agitation period in an ice bath
  4. customwas removed by suction filtration
  5. washwashed with a small amount of tetrahydrofuran
  6. customDrying

Sources & evidence

ORD record
ord-ac03e1f6dd6748bb97e1e6632df1794a
Source dataset
uspto-grants-2007_03
Patent number
US07195649B2

Reaction notes

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