Hydrazine hydrate (1:1) → 4-Methoxypyridine-2-carbohydrazide

HRID 985527Notes

Reaction equation

HRID 985527 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][N:6]=1)=O.O.[NH2:14][NH2:15]>CO>[CH3:12][O:11][C:9]1[CH:8]=[CH:7][N:6]=[C:5]([C:3]([NH:14][NH2:15])=[O:2])[CH:10]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 1519345Methyl 4-methoxypyridine-2-carboxylate

Product 1

HCID 109539124-Methoxypyridine-2-carbohydrazideYield 81%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

4-Methoxypyridine-2-carboxylic acid methyl ester (17.6 g, 0.105 mol) was dissolved in methanol (100 ml) and cooled to 0° C. before adding hydrazine hydrate (21 ml) dropwise over 10 min. The mixture was then refrigerated at 4° C. for 16 h. The resulting solid was filtered, washed with cold methanol and dried to afford 4-methoxypyridine-2-carboxylic acid hydrazide (14.3 g, 81%) as a white powder. 1H NMR (360 MHz, CDCl3) δH 3.89 (3H, s), 4.55 (2H, br s), 7.12 (1H, dd, J 3 and 6), 7.50 (1H, d, J 3), 8.42 (1H, d, J 6), 9.79 (1H, br s).

Workup

  1. filtrationThe resulting solid was filtered
  2. washwashed with cold methanol
  3. customdried

Sources & evidence

ORD record
ord-aad7553ededf41d6a75d2fa013f7d7a1
Source dataset
uspto-grants-2005_03
Patent number
US06872731B2

Reaction notes

Loading…