Hydrazine hydrate (1:1) → HCID 66959007, compound

HRID 2283793Notes

Reaction equation

HRID 2283793 reaction equation
O.NN.[Br:4][C:5]1[C:6]([C:24]#[N:25])=[N:7][N:8]([CH3:23])[C:9]=1[CH2:10][CH2:11][N:12]1C(=O)C2C(=CC=CC=2)C1=O>C(O)C>[NH2:12][CH2:11][CH2:10][C:9]1[N:8]([CH3:23])[N:7]=[C:6]([C:24]#[N:25])[C:5]=1[Br:4]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 66958959HCID 66958959, compound

Product 1

HCID 66959007HCID 66959007, compoundYield 98.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of hydrazine hydrate (6.40 g, 127 mmol) and 4-bromo-5-[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl]-1-methyl-1H-pyrazole-3-carbonitrile (9.15 g, 25.5 mmol) in ethanol (200 mL) was heated at reflux for 80 minutes, then was allowed to cool to ambient temperature in a water bath. A precipitate formed and was isolated by filtration and washed with cold ethanol. The filtrate was concentrated under reduced pressure, and the resulting white solid was twice treated with toluene and concentrated under reduced pressure then dried under vacuum to provide 5.74 g of 5-(2-aminoethyl)-4-bromo-1-methyl-1H-pyrazole-3-carbonitrile as an off-white solid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 80 minutes
  3. customA precipitate formed
  4. customwas isolated by filtration
  5. washwashed with cold ethanol
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. additionthe resulting white solid was twice treated with toluene
  8. concentrationconcentrated under reduced pressure
  9. customthen dried under vacuum

Sources & evidence

ORD record
ord-1ec144a010cd439798966038dcebdaa4
Source dataset
uspto-grants-2015_09
Patent number
US09145410B2

Reaction notes

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