Nitric Acid → HCID 12109159, compound

HRID 619249Notes

Reaction equation

HRID 619249 reaction equation
[C:1]([NH:4][C@@H:5]([C:7]1[CH:16]=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][CH:8]=1)[CH3:6])(=[O:3])[CH3:2].[N+:17]([O-])([OH:19])=[O:18].S(=O)(=O)(O)O>>[C:1]([NH:4][C@@H:5]([C:7]1[CH:16]=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][C:8]=1[N+:17]([O-:19])=[O:18])[CH3:6])(=[O:3])[CH3:2]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 12109158HCID 12109158, compound

Product 1

HCID 12109159HCID 12109159, compound

Procedure

Methyl (R)-4-(1-acetamidoethyl)benzoate (2 g) was added portionwise to a mixed solution of conc. nitric acid (1.2 ml) and conc. sulfuric acid (1.2 ml) under ice-cooling, and the mixture was stirred at room temperature for 5 hours. The reaction mixture was poured into ice-water, and extracted with chloroform. The extract was washed with water, dried, and concentrated under reduced pressure. The obtained crystals were recrystallized from ethyl acetate-hexane to give 1.4 g of methyl (R)-4-(1-acetamidoethyl)-3-nitrobenzoate.

Workup

  1. temperaturecooling
  2. extractionextracted with chloroform
  3. washThe extract was washed with water
  4. customdried
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained crystals were recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-f3bc926cb941469daf3ad23a9fd503fa
Source dataset
uspto-grants-1999_09
Patent number
US05958944

Reaction notes

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