Hydrazine → HCID 178508048, compound

HRID 1466570Notes

Reaction equation

HRID 1466570 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8](=O)[C:9]([N:14]2C(=O)C3C(=CC=CC=3)C2=O)=[CH:10][N:11](C)C)[CH:5]=[CH:6][CH:7]=1.[NH2:26]N>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:9]([NH2:14])=[CH:10][NH:11][N:26]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 666775102-(3-(3-Chlorophenyl)-1-(dimethylamino)-3-oxoprop-1-en-2-yl)isoindoline-1,3-dione

Product 1

HCID 178508048HCID 178508048, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-(3-(3-chlorophenyl)-1-(dimethylamino)-3-oxoprop-1-en-2-yl)isoindoline-1,3-dione (255 mg, 0.719 mmol, 1 eq) and hydrazine (0.15 mL, 4.8 mmol, 6.6 eq) in 10 mL ethanol was stirred under reflux for 2 hours. The ethanol and excess hydrazine were removed under vacuum. The crude product was purified by flash chromatography on silica gel (50 to 100% ethyl acetate in heptanes) to yield 111.4 mg (80%) of 3-(3-chlorophenyl)-1H-pyrazol-4-amine LCMS (ESI) m+H=194.0; 1H NMR (400 MHz, CD3OD) δ: 7.75 (broad, 1H), 7.65 (broad, 1H), 7.41 (t, 1H), 7.32 and 7.30 (overlapping s and s, 2H).

Workup

  1. temperatureunder reflux for 2 hours
  2. customThe ethanol and excess hydrazine were removed under vacuum
  3. customThe crude product was purified by flash chromatography on silica gel (50 to 100% ethyl acetate in heptanes)

Sources & evidence

ORD record
ord-eb75f27a7ac24b6da9c58ba90fac94c7
Source dataset
uspto-grants-2015_04
Patent number
US08999998B2

Reaction notes

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