Toluene → HCID 66916890, compound

HRID 453266Notes

Reaction equation

HRID 453266 reaction equation
[NH2:1][NH2:2].[C:3]([O-])([O-])=O.[K+].[K+].[C:9]([O:12][CH2:13][CH3:14])(=O)C.C(O[C:19](=[O:21])[CH3:20])(=O)C.[C:22]1([CH3:28])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>O>[CH3:9][O:12][C:13]1[CH:14]=[CH:3][CH:28]=[C:22]2[C:27]=1[CH:26]=[CH:25][C:24]([NH:1][NH:2][C:19](=[O:21])[CH3:20])=[CH:23]2

Participants

7

Reactant 5

HCID 1140TolueneHCID 7918Acetic AnhydrideHCID 8857Ethyl AcetateHCID 9321HydrazineHCID 11430Potassium Carbonate

Product 1

HCID 66916890HCID 66916890, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The hydrazine chlorhydrate (1.55 g, 6.9 mmol) was suspended in water (25 ml), K2CO3 (1 g) and ethyl acetate (25 ml) were added and it was energically shaken during 30 minutes. The phases were separated, the organic phase was washed with water, dried over Na2SO4, filtered, and evaporated to dryness resulting in 1.26 g of hydrazine base in a dark solid form. This solid was dissolved in anhydrous toluene (25 ml) and acetic anhydride (0.75 g, 7.4 mmol) was added keeping at stirring during 1 hr. Subsequently, petroleum ether was added and was left to rest in the fridge during 2 hrs. It was filtered and washed with more petroleum ether resulting, once dried, in 1.1 g (71%) of N′-(5-methoxynaphthalen-2-yl)acetohydrazide in the form of a reddish coloured solid, with a purity of 94% (HPLC).

Workup

  1. customThe phases were separated
  2. washthe organic phase was washed with water
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customresulting in 1.26 g of hydrazine base in a dark solid form
  7. stirringat stirring during 1 hr
  8. waitwas left
  9. waitto rest in the fridge during 2 hrs
  10. filtrationIt was filtered
  11. washwashed with more petroleum ether resulting
  12. dry with materialonce dried, in 1.1 g (71%) of N′-(5-methoxynaphthalen-2-yl)acetohydrazide in the form of a reddish coloured solid, with a purity of 94% (HPLC)

Sources & evidence

ORD record
ord-377b4f7e778044b8bff3e918f0965a4a
Source dataset
uspto-grants-2013_07
Patent number
US08492425B2

Reaction notes

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