Nitric Acid → HCID 67063017, compound

HRID 599267Notes

Reaction equation

HRID 599267 reaction equation
[N+:1]([O-:4])(O)=[O:2].[F:5][C:6]1[CH:11]=[CH:10][C:9]([C:12](=[O:18])[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:8]([CH3:19])[CH:7]=1>OS(O)(=O)=O>[F:5][C:6]1[C:11]([N+:1]([O-:4])=[O:2])=[CH:10][C:9]([C:12](=[O:18])[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:8]([CH3:19])[CH:7]=1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 24722272Ethyl 4-fluoro-2-methyl-α-oxobenzeneacetate

Product 1

HCID 67063017HCID 67063017, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
0 °C

Procedure

HNO3 (6.92 g, 71.4 mmol) was added dropwise to a suspension of ethyl 2-(4-fluoro-2-methylphenyl)-2-oxoacetate (15 g, 71.4 mmol) in conc. H2SO4 (50 mL) at ° C. After complete addition the resulting mixture was stirred at 0° C. for 30 min. The mixture was poured into ice water, and extracted with EtOAc. The organic extract was washed with brine, dried (MgSO4) and concentrated in vacuo to give ethyl 2-(4-fluoro-2-methyl-5-nitrophenyl)-2-oxoacetate (15 g, 83% yield), which was used in the next step without further purification. 1H NMR (400 MHz, CDCl3): δ 8.53 (d, J=7.2 Hz, 1 H), 7.24 (d, J=7.2 Hz, 1 H), 4.47 (q, J=7.2 Hz, 2 H), 2.67 (s, 3 H), 1.43 (t, J=7.2 Hz, 3 H).

Workup

  1. additionAfter complete addition the resulting mixture
  2. extractionextracted with EtOAc
  3. extractionThe organic extract
  4. washwas washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a4cef04c2ead4234a696ed5236b702da
Source dataset
uspto-grants-2011_03
Patent number
US07897762B2

Reaction notes

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