Hydrazine hydrate (1:1) → 2-Hydrazinyl-3-methylpyrazine

HRID 1098128Notes

Reaction equation

HRID 1098128 reaction equation
O.[NH2:2][NH2:3].Cl[C:5]1[C:10]([CH3:11])=[N:9][CH:8]=[CH:7][N:6]=1>C(O)C>[NH:2]([C:5]1[C:10]([CH3:11])=[N:9][CH:8]=[CH:7][N:6]=1)[NH2:3]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 66769Pyrazine, 2-chloro-3-methyl-

Product 1

HCID 2707022-Hydrazinyl-3-methylpyrazineYield 80%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

Hydrazine hydrate (9.66 mL, 311.14 mmol) was added to 2-chloro-3-methylpyrazine (CAS no. 95-58-9) (8 g, 62.23 mmol) in ethanol (25 mL). The resulting solution was stirred at 90° C. for 16 hours. The resulting solution was evaporated to dryness and the crude product was purified by crystallisation from toluene (125 mL) to afford 2-hydrazinyl-3-methylpyrazine (6.2 g, 80%). 1H NMR (400 MHz, DMSO-d6) δ 2.24 (3H, s), 7.61 (1H, d), 7.61 (1H, d), 7.87 (1H, d).

Workup

  1. customThe resulting solution was evaporated to dryness
  2. customthe crude product was purified by crystallisation from toluene (125 mL)

Sources & evidence

ORD record
ord-eba063b6363646cba6df39603f4ff3dc
Source dataset
uspto-grants-2012_03
Patent number
US08143263B2

Reaction notes

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