Hydrazine hydrate (1:1) → HCID 86717333, compound

HRID 2205843Notes

Reaction equation

HRID 2205843 reaction equation
[CH3:1][N:2]1[C:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[C:5]([C:13]#[C:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:4]([N:21]2C(=O)C3C(=CC=CC=3)C2=O)=[N:3]1.O.NN>C(O)C>[CH3:1][N:2]1[C:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[C:5]([C:13]#[C:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:4]([NH2:21])=[N:3]1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 86717331HCID 86717331, compound

Product 1

HCID 86717333HCID 86717333, compoundYield 74.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 2-[1-methyl-5-phenyl-4-(2-phenylethynyl)pyrazol-3-yl]isoindoline-1,3-dione (300 mg, 0.74 mmol), ethanol (5 mL) and hydrazine hydrate (56 μL, 1.11 mL) was stirred in a sealed tube at 90° C. for 1 h and cooled to room temperature. The reaction mixture was filtered. The filtrate was concentrated in vacuo and purified by column chromatography (silica gel, isohexane/ethyl acetate 7:3 to 1:1) yielding the title compound as a solid (150 mg).

Workup

  1. temperaturecooled to room temperature
  2. filtrationThe reaction mixture was filtered
  3. concentrationThe filtrate was concentrated in vacuo
  4. custompurified by column chromatography (silica gel, isohexane/ethyl acetate 7:3 to 1:1)

Sources & evidence

ORD record
ord-6f1cc509d8f248a1bf608220e5318e2b
Source dataset
uspto-grants-2016_06
Patent number
US09371332B2

Reaction notes

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