Methanol → 2-Methoxyisonicotinohydrazide

HRID 1478099Notes

Reaction equation

HRID 1478099 reaction equation
ClC1C=C(Cl)[CH:15]=[CH:14][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=CC=CC=1Cl)=[O:5].[OH2:19].[NH2:20][NH2:21].[CH3:22]O>>[CH3:22][O:5][C:4]1[CH:3]=[C:14]([C:15]([NH:20][NH2:21])=[O:19])[CH:12]=[CH:7][N:6]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24654Hydrazine hydrate (1:1)HCID 3467412,4-Dichloro-N-(2-chlorophenyl)benzamide

Product 1

HCID 3225512-Methoxyisonicotinohydrazide

Procedure

To a solution of 2-methoxypyridine-4-carboxylic acid 1 (1.0 g, 6.5 mmol) in CH3OH (30 mL) was added a few drops of SOCl2 at ambient temperature. The mixture was stirred under reflux for 16 hours and concentrated to give methyl 2-methoxypyridine-4-carboxylate 2. To the solution of 2-methoxypyridine-4-carboxylate 2 in CH3OH was added hydrazine monohydrate (2.0 mL, 37 mmol) at ambient temperature. The reaction mixture was stirred at ambient temperature for 16 hours and concentrated to give 2-methoxypyridine-4-carbohydrazide 3 as a white solid. Yield: 0.87 g, 80%.

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-c68bd6c4da994f869391afe177808daa
Source dataset
uspto-grants-2016_08
Patent number
US09403812B2

Reaction notes

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