Hydrazine → (E)-2-Hydrazino-but-2-enedioic acid dimethyl ester

HRID 1695376Notes

Reaction equation

HRID 1695376 reaction equation
[CH3:1][O:2][C:3]([C:5]#[C:6][C:7]([O:9][CH3:10])=[O:8])=[O:4].[NH2:11][NH2:12]>C(OCC)C.C1COCC1>[CH3:1][O:2][C:3](=[O:4])/[C:5](/[NH:11][NH2:12])=[CH:6]\[C:7]([O:9][CH3:10])=[O:8]

Participants

5

Reactant 2

HCID 9321HydrazineHCID 12980Dimethyl acetylenedicarboxylate

Product 1

HCID 55298578(E)-2-Hydrazino-but-2-enedioic acid dimethyl esterYield 35%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of dimethylacetylene dicarboxylate (1.4 g, 9.9 mmol) in diethylether (40 mL) under argon was added a solution of hydrazine in THF (1 M, 10 mL) and the resulting mixture stirred at room temperature overnight. The precipitate was filtered off and dried to afford the title compound (597 mg, 35%) as a white solid. MS: m/e=175.2 [M+H]+.

Workup

  1. filtrationThe precipitate was filtered off
  2. customdried

Sources & evidence

ORD record
ord-3efd8df7b605465a954d1066e18c2d68
Source dataset
uspto-grants-2012_04
Patent number
US08163728B2

Reaction notes

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