Hydrochloric Acid → HCID 178518877, compound

HRID 1423017Notes

Reaction equation

HRID 1423017 reaction equation
C([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)[C:10]=1[CH:11](OCC)OCC)=O)C.O.[NH2:26][NH2:27].Cl>C(O)(=O)C.O>[F:24][C:21]1[CH:22]=[CH:23][C:18]([N:9]2[C:10]3=[CH:11][N:26]=[N:27][C:4]([OH:3])=[C:6]3[CH:7]=[N:8]2)=[CH:19][CH:20]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 24654Hydrazine hydrate (1:1)HCID 67199165HCID 67199165, compound

Product 1

HCID 178518877HCID 178518877, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To a solution of 5-diethoxymethyl-1-(4-fluorophenyl)-1H-pyrazole-4-carboxylic acid ethyl ester (5.70 g, 16.9 mmol) in acetic acid (100 mL) is added hydrazine monohydrate (5.0 mL, 6.1 mmol) and 12 N aqueous hydrochloric acid (200 μL). The reaction mixture is warmed at reflux. After 2 hours, the mixture is cooled to room temperature and diluted with water. The solid is collected by filtration, washed with water and air dried to afford 1-(4-fluorophenyl)-1H-pyrazolo[3,4-d]pyridazin-4-ol.

Workup

  1. temperatureThe reaction mixture is warmed
  2. temperatureat reflux
  3. filtrationThe solid is collected by filtration
  4. washwashed with water and air
  5. customdried

Sources & evidence

ORD record
ord-fb2fa65d28624fb18008eaceded75db2
Source dataset
uspto-grants-2015_01
Patent number
US08927550B2

Reaction notes

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