Ammonium Chloride → HCID 66851699, compound

HRID 1466597Notes

Reaction equation

HRID 1466597 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:21][CH3:22])=[C:6]([C:8]2[N:12]([CH2:13][CH2:14][CH:15]([CH3:17])[CH3:16])[N:11]=[CH:10][C:9]=2[N+:18]([O-])=O)[CH:7]=1.[Cl-].[NH4+]>C(O)C.O.[Fe]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:21][CH3:22])=[C:6]([C:8]2[N:12]([CH2:13][CH2:14][CH:15]([CH3:17])[CH3:16])[N:11]=[CH:10][C:9]=2[NH2:18])[CH:7]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 66863438HCID 66863438, compound

Product 1

HCID 66851699HCID 66851699, compound

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of 5-(5-Chloro-2-methoxyphenyl)-1-isopentyl-4-nitro-1H-pyrazole (632 mg, 1.95 mmol, 1.00 eq), iron (642.5 mg, 11.50 mmol, 5.90 eq), and ammonium chloride (500.7 mg, 9.36 mmol, 4.80 eq) in 5.0 mL ethanol and 10 mL water was stirred at 75° C. for 2 hours. The reaction mixture was concentrated, 10 mL of saturated bicarbonate solution was added, and the aqueous layer was extracted with dichloromethane (20 mL*3). The combined dichloromethane layers were dried with magnesium sulfate, filtered and concentrated. The reddish yellow oil was used as is for the next step LCMS (ESI) m+H=293.8.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. addition10 mL of saturated bicarbonate solution was added
  3. extractionthe aqueous layer was extracted with dichloromethane (20 mL*3)
  4. dry with materialThe combined dichloromethane layers were dried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e007ac8a1a05434cb52fb581109214d1
Source dataset
uspto-grants-2015_04
Patent number
US08999998B2

Reaction notes

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