Hydrazine hydrate (1:1) → HCID 66678705, compound

HRID 1025989Notes

Reaction equation

HRID 1025989 reaction equation
[CH:1]1([CH2:4][N:5]2[CH:9]=[CH:8][C:7]([CH2:10][N:11]3C(=O)C4C(=CC=CC=4)C3=O)=[N:6]2)[CH2:3][CH2:2]1.O.NN>C1COCC1.C(O)C.C(OC)(C)(C)C>[CH:1]1([CH2:4][N:5]2[CH:9]=[CH:8][C:7]([CH2:10][NH2:11])=[N:6]2)[CH2:2][CH2:3]1

Participants

6

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 66678614HCID 66678614, compound

Product 1

HCID 66678705HCID 66678705, compoundYield 92%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

To a colorless solution of 2-((1-(cyclopropylmethyl)-1H-pyrazol-3-yl)methyl)isoindoline-1,3-dione (example BV; 400 mg, 1.42 mmol) in THF (10 mL) and ethanol (5 mL) was added hydrazine hydrate (0.62 g, 0.60 mL, 12.3 mmol). The white suspension was stirred for 20 h at room temperature, diluted with t-butylmethyl ether (50 mL) and phtalyl hydrazide was removed by filtration. The filtrate was concentrated in vacuo and the crude material was purified by flash chromatography (amino phase, 12 g, 0% to 100% ethyl acetate in heptane) to yield 197 mg (92%) of the title compound as a light yellow oil; MS (EI): 152.1 (M+H)+.

Workup

  1. customwas removed by filtration
  2. concentrationThe filtrate was concentrated in vacuo
  3. customthe crude material was purified by flash chromatography (amino phase, 12 g, 0% to 100% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-e734fb6966ab4da7a17769a6acdf6741
Source dataset
uspto-grants-2014_05
Patent number
US08729105B2

Reaction notes

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