Hydrazinium chloride → HCID 64591821, compound

HRID 1520776Notes

Reaction equation

HRID 1520776 reaction equation
C[O:2][C:3]([C:5]1[NH:6][N:7]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH:17]([F:19])[F:18])[CH:11]=2)[CH:9]=1)=[O:4].FC(F)OC1C=C(C(=O)/C=C(\O)/C(OC)=O)C=CC=1.Cl.NN>C(O)C>[F:19][CH:17]([F:18])[O:16][C:12]1[CH:11]=[C:10]([C:8]2[CH:9]=[C:5]([C:3]([OH:4])=[O:2])[NH:6][N:7]=2)[CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 115031Hydrazinium chlorideHCID 71087808HCID 71087808, compoundHCID 178501819HCID 178501819, compound

Product 1

HCID 64591821HCID 64591821, compoundYield 79.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5-(3-Difluoromethoxy-phenyl)-2H-pyrazole-3-carboxylic acid methyl ester: To a solution of (Z)-methyl 4-(3-(difluoromethoxy)phenyl)-2-hydroxy-4-oxobut-2-enoate (CAS-832741-03-4) (800 mg, 2.94 mmol, Eq: 1.00) in Ethanol (20 ml) was added Hydrazine hydrochloride (220 mg, 3.21 mmol, Eq: 1.093) at rt to give an orange suspension. The resulting mixture was stirred overnight at the same temperature. After 1 day the reaction was complete. After stirring the solvent was removed under reduce pressure and to the mixture was added brine, the solution was extracted two times with AcOEt, and the combined organic layers were dried over MgSO4, filtered and concentrated to give the desired compound as a light-brown solid (630 mg, 79.9%). MS (ISP): 269.0 ([M+H]+).

Workup

  1. customto give an orange suspension
  2. waitAfter 1 day the reaction was complete
  3. stirringAfter stirring the solvent
  4. customwas removed
  5. additionto the mixture was added brine
  6. extractionthe solution was extracted two times with AcOEt
  7. dry with materialthe combined organic layers were dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-f1ee5df22cf84a418fed1ea72d97e7d3
Source dataset
uspto-grants-2015_07
Patent number
US09073911B2

Reaction notes

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