Hydrazine hydrate (1:1) → HCID 68406318, compound

HRID 1786185Notes

Reaction equation

HRID 1786185 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]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 59186967HCID 59186967, compound

Product 1

HCID 68406318HCID 68406318, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

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

  1. temperaturethe resulting mixture was then heated
  2. temperatureunder reflux for 20 h
  3. 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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