Hydrazine hydrate (1:1) → 2-Methoxyisonicotinohydrazide

HRID 500543Notes

Reaction equation

HRID 500543 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][N:7]=[C:6]([O:10][CH3:11])[CH:5]=1.O.[NH2:14][NH2:15]>C(O)C>[CH3:11][O:10][C:6]1[CH:5]=[C:4]([CH:9]=[CH:8][N:7]=1)[C:3]([NH:14][NH2:15])=[O:2]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 14223465Methyl 2-methoxyisonicotinate

Product 1

HCID 3225512-MethoxyisonicotinohydrazideYield 80.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
75 °C

Procedure

2-Methoxy-isonicotinic acid methyl ester (23.0 g, 137 mmol) and hydrazine hydrate (8.95 g, 178 mmol) were dissolved in ethanol and stirred at 75° C. for 12 hours. The reaction mixture was concentrated and the remaining solid was tritiated in hexanes/ether (80:20), filtered and dried to afford the title compound as a solid (18.4 g, 80%).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. filtrationfiltered
  3. customdried

Sources & evidence

ORD record
ord-7a2aeb8ffa114dd899881945ec8d3c9d
Source dataset
uspto-grants-2010_08
Patent number
US07772235B2

Reaction notes

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