Hydrazine hydrate (1:1) → Oxane-4-carbohydrazide

HRID 541258Notes

Reaction equation

HRID 541258 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([C:7]([O:9]C)=O)[CH2:3][CH2:2]1.O.[NH2:12][NH2:13]>CO>[O:1]1[CH2:6][CH2:5][CH:4]([C:7]([NH:12][NH2:13])=[O:9])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 27735202H-Pyran-4-carboxylic acid, tetrahydro-, methyl ester2×

Product 1

HCID 28064717Oxane-4-carbohydrazideYield 88.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a round-bottom flask was added a solution of methyl tetrahydro-2H-pyran-4-carboxylate (compound 137.1, 5.00 g, 31.2 mmol, 1.00 equiv, 90%) in methanol (50 mL). Hydrazine hydrate (5.20 g, 83.2 mmol, 3.00 equiv) was added and the resulting mixture was stiffed overnight at 40° C. in an oil bath. After cooling to ambient temperature, the mixture was concentrated in vacuo to yield 4.00 g (80%) of tetrahydro-2H-pyran-4-carbohydrazide as a white solid.

Workup

  1. concentrationthe mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-fb3ec367589d46d9bb1560b3294d1bc3
Source dataset
uspto-grants-2014_10
Patent number
US08871790B2

Reaction notes

Loading…