N-bromobutanimide → Ethyl (6-methoxy-2-nitrobenzyl)aminoacetate

HRID 2417509Notes

Reaction equation

HRID 2417509 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([N+:9]([O-:11])=[O:10])[C:4]=1[CH3:12].C1C(C(OO)=O)=CC=CC=1.BrN1C(=O)CCC1=O.Cl.[CH2:32]([O:34][C:35](=[O:38])[CH2:36][NH2:37])[CH3:33].C(=O)([O-])O.[Na+]>C(O)C.C(OCC)(=O)C.C1C=CC=CC=1>[CH3:1][O:2][C:3]1[C:4]([CH2:12][NH:37][CH2:36][C:35]([O:34][CH2:32][CH3:33])=[O:38])=[C:5]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:7][CH:8]=1

Participants

9

Reactant 5

HCID 67184N-bromobutanimideHCID 785542-Methyl-3-nitroanisoleHCID 516892Sodium BicarbonateHCID 523077Perbenzoic acidHCID 2723640Glycine ethyl ester, hydrochloride

Product 1

HCID 86589881Ethyl (6-methoxy-2-nitrobenzyl)aminoacetate

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

5.0 g (29 mmol) of 1-methoxy-2-methyl-3-nitrobenzene was added to a mixture of 50 ml of benzene, 50 ml of perbenzoic acid and 8 g (45 mmol) of N-bromosuccinimide, and they were stirred at 80° C. for one day. After the treatment with ethyl acetate as the extracting solvent by an ordinary method, the obtained crude product was dissolved in 50 ml of ethanol. 8.4 g (60 mmol) of glycine ethyl ester hydrochloride and 5.0 g (60 mmol) of sodium hydrogencarbonate were added to the obtained solution, and they were stirred at 70° C. overnight. The solvent was evaporated. After the extraction with ethyl acetate, the obtained extract was washed 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. stirringwere stirred at 70° C. overnight
  2. customThe solvent was evaporated
  3. extractionAfter the extraction with ethyl acetate
  4. extractionthe obtained extract
  5. washwas washed with 1 N hydrochloric acid
  6. extractionAfter the extraction with ethyl acetate
  7. washthe obtained organic layer was washed with saturated aqueous sodium chloride solution
  8. customdried
  9. customThe solvent was evaporated

Sources & evidence

ORD record
ord-945c0c297c304604985e18d610912f56
Source dataset
uspto-grants-2004_11
Patent number
US06825191B2

Reaction notes

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