2-Furancarboxylic acid, hydrazide → HCID 66776522, compound

HRID 1644168Notes

Reaction equation

HRID 1644168 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([NH:8][NH2:9])=[O:7].[CH3:10][C:11](=[CH:13][CH2:14][CH2:15][C@H:16]([CH2:18][CH:19]=O)[CH3:17])[CH3:12]>C(O)C>[CH3:17][C@H:16]([CH2:15][CH2:14][CH:13]=[C:11]([CH3:12])[CH3:10])[CH2:18][CH:19]=[N:9][NH:8][C:6]([C:2]1[O:1][CH:5]=[CH:4][CH:3]=1)=[O:7]

Participants

4

Reactant 2

HCID 187312-Furancarboxylic acid, hydrazideHCID 754276-Octenal, 3,7-dimethyl-, (3R)-

Product 1

HCID 66776522HCID 66776522, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2a (1.50 g, 11.9 mmol) and (R)-citronellal (2.74 g, 17.7 mmol) in ethanol (30 ml) was heated under reflux for 2 h. After cooling to room temperature, the product was concentrated and the excess of citronellal removed by Kugelrohr distillation (120° C., 0.39 mbar) to give 2.03 g (55%) of a yellow solid as a mixture of two isomers (ca. 7:1).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 h
  3. concentrationthe product was concentrated
  4. customthe excess of citronellal removed by Kugelrohr distillation (120° C., 0.39 mbar)

Sources & evidence

ORD record
ord-6715a1c156aa40dfbdb36ce08ed2eed7
Source dataset
uspto-grants-2012_02
Patent number
US08124578B2

Reaction notes

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