Hydrazine hydrate (1:1) → HCID 68406318, compound
Reaction equation
C([O:3][C:4](=O)[CH2:5][C:6]1[CH:7]=[N:8][C:9]([CH3:12])=[CH:10][CH:11]=1)C.O.[NH2:15][NH2:16]>C(O)CCC>[CH3:12][C:9]1[N:8]=[CH:7][C:6]([CH2:5][C:4]([NH:15][NH2:16])=[O:3])=[CH:11][CH:10]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
As described for example 112a, (6-methyl-pyridin-3-yl)-acetic acid ethyl ester in butanol was reacted with hydrazine hydrate (2 equivalents) and the resulting mixture was then heated under reflux for 20 h. Evaporation of all volatiles and crystallization from n-butanol and toluene afforded the title compound as a white solid (yield: 72%). 1H-NMR (300 MHz, DMSO): δ=2.42 (s, 3H), 3.32 (s, 2H), 4.21 (s, 2H), 7.17 (d, J=8 Hz, 1H), 7.53 (dd, J=2 Hz, J=8 Hz, 1H), 8.30 (d, J=2 Hz, 1H), 9.23 (s, 1H).
Workup
- temperaturethe resulting mixture was then heated
- temperatureunder reflux for 20 h
- customEvaporation of all volatiles and crystallization from n-butanol and toluene
Sources & evidence
- ORD record
- ord-fc87e9f8a2654a88b7073a18c13fa270
- Source dataset
- uspto-grants-2009_03
- Patent number
- US07507729B2
Reaction notes
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