2-Chloro-6-nitrotoluene → HCID 63746644, compound

HRID 2417467Notes

Reaction equation

HRID 2417467 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-:10])=[O:9])[C:3]=1[CH3:11].C1C(C(OO)=O)=CC=CC=1.BrN1C(=O)CCC1=O.Cl.[CH2:31]([O:33][C:34](=[O:37])[CH2:35][NH2:36])[CH3:32].C(=O)([O-])O.[Na+]>C1C=CC=CC=1.C(O)C.C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-:10])=[O:9])[C:3]=1[CH2:11][NH:36][CH2:35][C:34]([O:33][CH2:31][CH3:32])=[O:37]

Participants

9

Reactant 5

HCID 67402-Chloro-6-nitrotolueneHCID 67184N-bromobutanimideHCID 516892Sodium BicarbonateHCID 523077Perbenzoic acidHCID 2723640Glycine ethyl ester, hydrochloride

Product 1

HCID 63746644HCID 63746644, compound

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

4.84 g (28.3 mmol) of 2-chloro-6-nitrotoluene was dissolved in 50 ml of benzene. 50 mg of perbenzoic acid and 6.0 g (34 mmol) of N-bromosuccinimide were added to the obtained solution, and the obtained solution was stirred at 80° C. overnight. The reaction solution was treated with ethyl acetate as the extracting solvent by an ordinary method to obtain the crude product. The crude product was dissolved in 100 ml of ethanol. 11.9 g (84.9 mmol) of glycine ethyl ester hydrochloride and 8.9 g (106 mmol) of sodium hydrogencarbonate were added to the obtained solution, and they were stirred at 80° C. for 4 hours. The insoluble matter was removed by the filtration, and the solvent was evaporated. After the extraction with ethyl acetate followed by washing with 1 N hydrochloric acid, the obtained aqueous layer was made basic with 1 N sodium hydroxide. After the extraction with ethyl acetate, the obtained organic layer was washed with saturated aqueous sodium chloride solution and then dried. The solvent was evaporated to obtain the title compound.

Workup

  1. customto obtain the crude product
  2. stirringwere stirred at 80° C. for 4 hours
  3. customThe insoluble matter was removed by the filtration
  4. customthe solvent was evaporated
  5. extractionAfter the extraction with ethyl acetate
  6. washby washing with 1 N hydrochloric acid
  7. extractionAfter the extraction with ethyl acetate
  8. washthe obtained organic layer was washed with saturated aqueous sodium chloride solution
  9. customdried
  10. customThe solvent was evaporated

Sources & evidence

ORD record
ord-15240d4491ea4b968f2605f071f4855d
Source dataset
uspto-grants-2004_11
Patent number
US06825191B2

Reaction notes

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