Hydrochloric Acid → HCID 73461792, compound

HRID 992477Notes

Reaction equation

HRID 992477 reaction equation
[CH3:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.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:8]=[CH:7][C:5]([NH:6][N:13]=[C:18]([CH3:17])[C:19]([O:21][CH2:22][CH3:23])=[O:20])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1

Participants

8

Reactant 5

HCID 313Hydrochloric Acid2×HCID 701Ethyl 2-methylacetoacetateHCID 69784-Methyl-2-nitroanilineHCID 14797Potassium HydroxideHCID 23668193Sodium Nitrite

Product 1

HCID 73461792HCID 73461792, compoundYield 88.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

Into 110 ml of water was suspended 30.00 g (0.197 mol) of 4-methyl-2-nitroaniline followed by adding 66 ml of concentrated hydrochloric acid thereto. An aqueous solution (35 ml) of 16.33 g (0.237 mol) of sodium nitrite was added dropwise thereinto at 10° C. or below, followed by stirring for 40 minutes under ice-cooling to prepare a diazonium salt solution. In a mixed solution of 150 ml of ethanol and 300 ml of water was dissolved 28.43 g (0.197 mol) of ethyl 2-methylacetoacetate, followed by adding 120 ml of an aqueous solution of 53.36 g (0.808 mol) of potassium hydroxide thereto under ice-cooling. Then, the previously-prepared diazonium salt solution was added dropwise thereinto at the same temperature and stirred under ice-cooling for 20 minutes. After concentrated hydrochloric acid was added thereto to adjust to pH 1, the resulting precipitates were collected by filtration, washed with water and vacuum dried on phosphorus pentaoxide to give 46.42 g of the title compound.

Workup

  1. customat 10° C. or below
  2. temperaturecooling
  3. temperatureunder ice-cooling
  4. stirringat the same temperature and stirred under ice-
  5. temperaturecooling for 20 minutes
  6. customthe resulting precipitates
  7. filtrationwere collected by filtration
  8. washwashed with water and vacuum
  9. customdried on phosphorus pentaoxide

Sources & evidence

ORD record
ord-6a6b3a5b6fb14a06984b5990bd20351f
Source dataset
uspto-grants-2002_10
Patent number
US06469043B1

Reaction notes

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