1-(2-Hydrazino-4-pyridyl)-1-ethylenedioxyethane → 1-(2-Amino-4-pyridyl)-1-ethylenedioxyethane

HRID 1155536Notes

Reaction equation

HRID 1155536 reaction equation
[NH:1]([C:3]1[CH:8]=[C:7]([CH:9]2[O:14][CH2:13][CH2:12][O:11][CH2:10]2)[CH:6]=[CH:5][N:4]=1)N.[H][H]>[Ni].C(O)C>[NH2:1][C:3]1[CH:8]=[C:7]([CH:9]2[O:14][CH2:13][CH2:12][O:11][CH2:10]2)[CH:6]=[CH:5][N:4]=1

Participants

5

Reactant 2

HCID 705114241-(2-Hydrazino-4-pyridyl)-1-ethylenedioxyethaneHCID 178418361HCID 178418361, compound

Product 1

HCID 705124891-(2-Amino-4-pyridyl)-1-ethylenedioxyethane

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A mixture of 9.56 g. (49 mmoles) of 1-(2-hydrazino-4-pyridyl)-1-ethylenedioxyethane and 35 g. of Raney nickel in 150 ml. of absolute ethanol was shaken in a hydrogen atmosphere at an initial pressure of 3 atms. at room temperature for 4 hours. The catalyst was filtered and the filtrate concentrated to give 1-(2-amino-4-pyridyl)-1-ethylenedioxyethane as a white solid, m.p. 123°-126° C. The residual material was dissolved in 60 ml. of 2 N hydrochloric acid and heated at 75° C. for 3 hours. The mixture was cooled, neutralized with sodium bicarbonate and extracted with chloroform (30 ml.×6). The combined extracts were dried and concentrated to give a pale yellow solid, which on recrystallization from toluene gave 5.0 g. (75%) of 1-(2-amino-4-pyridyl)-1-ethanone, m.p. 133°-133.5° C.

Workup

  1. additionA mixture of 9.56 g
  2. filtrationThe catalyst was filtered
  3. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-3f42adadd4ec427a8a75fdb08bf5ed01
Source dataset
uspto-grants-1981_11
Patent number
US04302464

Reaction notes

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