Potassium Nitrate → (2-Acetamido-5-chloro-3-nitrophenyl)methyl acetate

HRID 1012116Notes

Reaction equation

HRID 1012116 reaction equation
[N+:1]([O-:4])([O-])=[O:2].[K+].[C:6]([NH:9][C:10]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:11]=1[CH2:12][O:13][C:14](=[O:16])[CH3:15])(=[O:8])[CH3:7]>OS(O)(=O)=O>[C:6]([NH:9][C:10]1[C:20]([N+:1]([O-:4])=[O:2])=[CH:19][C:18]([Cl:21])=[CH:17][C:11]=1[CH2:12][O:13][C:14](=[O:16])[CH3:15])(=[O:8])[CH3:7]

Participants

4

Reactant 2

HCID 24434Potassium NitrateHCID 67106565(2-Acetamido-5-chlorophenyl)methyl acetate

Product 1

HCID 67106404(2-Acetamido-5-chloro-3-nitrophenyl)methyl acetateYield 20%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
0 °C

Procedure

Potassium nitrate (1.01 g, 10 mmol) was added to conc. H2SO4 (10 ml) at 0° C. This mixture was stirred at 0° C. for 15 min, then acetic acid 2-acetylamino-5-chloro-benzyl ester (1.92 g, 8 mmol) was added in small portions over 15 min. The reaction mixture was stirred at 0° C. for a further 1 h, and then poured onto crushed ice. The precipitate formed was collected by filtration to give a mixture of isomers, which were separated by column chromatography eluting with a gradient of 0-60% ethyl acetate in petroleum ether to give the desired acetic acid 2-acetylamino-5-chloro-3-nitro-benzyl ester as a yellow solid (0.454 g, 20%).

Workup

  1. stirringThe reaction mixture was stirred at 0° C. for a further 1 h
  2. additionpoured
  3. customonto crushed ice
  4. customThe precipitate formed
  5. filtrationwas collected by filtration
  6. customto give
  7. additiona mixture of isomers, which
  8. customwere separated by column chromatography
  9. washeluting with a gradient of 0-60% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-8532a624d492465cb735f3152b73e7c0
Source dataset
uspto-grants-2011_07
Patent number
US07977477B2

Reaction notes

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