Hydrochloric Acid → Ethyl Pyruvate N-(5-methyl-2-nitrophenyl)hydrazone

HRID 1173086Notes

Reaction equation

HRID 1173086 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([CH:8]=1)[NH2:7].Cl.[N:13]([O-])=O.[Na+].[CH3:17][CH:18](C(C)=O)[C:19]([O:21][CH2:22][CH3:23])=[O:20].[OH-].[K+]>C(O)C.O>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([NH:7][N:13]=[C:18]([CH3:17])[C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:8]=1

Participants

8

Reactant 5

HCID 313Hydrochloric Acid2×HCID 701Ethyl 2-methylacetoacetateHCID 113566-Nitro-m-toluidineHCID 14797Potassium HydroxideHCID 23668193Sodium Nitrite

Product 1

HCID 85872281Ethyl Pyruvate N-(5-methyl-2-nitrophenyl)hydrazone

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

75.0 g (493 mmol) of 5-methyl-2-nitroaniline was added to a mixed solution of 160 ml of water and 170 ml of concentrated hydrochloric acid and the mixture was stirred. To the mixture was added dropwise 80 ml of an aqueous solution containing 36.0 g (517 mmol) of sodium nitrite at −20° C. The reaction solution was added to a solution obtained by dissolving ethyl 2-methylacetoacetate in 100 ml of ethanol and then adding 200 ml of a 12N aqueous potassium hydroxide thereto, at −20° C. over 30 minutes under stirring. After stirring at the same temperature for 30 minutes, 100 ml of concentrated hydrochloric acid was added thereto. The resulting precipitates were collected by filtration, washed with water and dried under reduced pressure overnight. A mixed solution of diethyl ether and hexane was added thereto and the crystals were collected by filtration, to give 130 g of the title compound.

Workup

  1. additionThe reaction solution was added to a solution
  2. customobtained
  3. stirringat −20° C. over 30 minutes under stirring
  4. stirringAfter stirring at the same temperature for 30 minutes
  5. customThe resulting precipitates
  6. filtrationwere collected by filtration
  7. washwashed with water
  8. customdried under reduced pressure overnight
  9. additionA mixed solution of diethyl ether and hexane was added
  10. filtrationthe crystals were collected by filtration

Sources & evidence

ORD record
ord-feea41a9eea6429dbefcae657ece3a61
Source dataset
uspto-grants-2010_11
Patent number
US07834049B2

Reaction notes

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