Hydrazine hydrate (1:1) → 2-Methylpyridine-3-carbohydrazide

HRID 576704

Reaction equation

HRID 576704 reaction equation
[CH3:1][C:2]1[N:12]=[CH:11][CH:10]=[CH:9][C:3]=1[C:4](OCC)=[O:5].O.[NH2:14][NH2:15]>CCO>[CH3:1][C:2]1[N:12]=[CH:11][CH:10]=[CH:9][C:3]=1[C:4]([NH:14][NH2:15])=[O:5]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 74401Ethyl 2-methylnicotinate

Product 1

HCID 450842992-Methylpyridine-3-carbohydrazideYield 99.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 2-methylnicotinate (500 mg, 3.0 mmol) in EtOH (2.3 mL) was added hydrazine monohydrate (0.3 mL, 6.1 mmol). The reaction mixture was heated at reflux for 3 days and then concentrated to afford the desired product as a beige solid (450 mg, 98%). MS (ESI): mass calcd. for C7H9N3O, 151.1; m/z found, 152.1 [M+H]+. 1H NMR (500 MHz, DMSO-d6) δ 9.57 (br s, 1H), 8.49 (dd, J=4.9, 1.8 Hz, 1H), 7.66 (dd, J=7.7, 1.7 Hz, 1H), 7.26 (ddd, J=7.7, 4.9, 0.5 Hz, 1H), 4.85-4.05 (bs, 2H), 2.50 (d, J=4.1 Hz, 3H).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 3 days
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-0f8d181823634d5daf1892c5d3ffad5e
Source dataset
uspto-grants-2015_05
Patent number
US09040534B2

Linked notes

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