Hydrazine hydrate (1:1) → HCID 178469062, compound

HRID 1671333Notes

Reaction equation

HRID 1671333 reaction equation
[C:1]([CH:5]([C:11]([O:13]CC)=O)[C:6]([O:8][CH2:9][CH3:10])=[O:7])(=O)[CH2:2][CH3:3].O.[NH2:17][NH2:18]>C(O)(=O)C.C(OCC)C>[CH2:9]([O:8][C:6]([C:5]1[C:1]([CH2:2][CH3:3])=[N:17][NH:18][C:11]=1[OH:13])=[O:7])[CH3:10]

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 307201,3-Diethyl 2-(1-oxopropyl)propanedioate

Product 1

HCID 178469062HCID 178469062, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
100 °C

Procedure

To diethyl propionylmalonate (3.63 g, 16.8 mmol) in glacial acetic acid (8 ml) at RT, is added hydrazine hydrate (55% hydrazine, 1.4 ml, 25.2 mmol). The reaction mixture is heated at 100° C. for 2 hrs and allowed to cool to ambient temperature whereupon crystallization occurs. The mixture is diluted with diethyl ether (approx. 25 ml) and stirred for 20 minutes and filtered to obtain the title compound as a white solid. This is washed with diethyl ether and dried in vacuo. A second crop of product is obtained by cooling the filtrate liquor, the precipitated solid is washed with diethyl ether and dried in vacuo. 1H NMR (400 MHz, DMSO-d6) δ 12.0 (1H, br s), 9.8 (1H, br s), 4.16 (2H, q, J 7.1), 2.73 (2H, q, J 7.5), 1.24 (3H, t, J 7.1), 1.14 (3H, t, J 7.5).

Workup

  1. temperatureto cool to ambient temperature whereupon crystallization
  2. filtrationfiltered

Sources & evidence

ORD record
ord-24abae911b894e7399d66dd6d3977822
Source dataset
uspto-grants-2011_08
Patent number
US07994203B2

Reaction notes

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