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

HRID 1360469Notes

Reaction equation

HRID 1360469 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-6b76f93b6cad4b14b54874eb8c390880
Source dataset
uspto-grants-2011_02
Patent number
US07879849B2

Reaction notes

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