Nitric Acid → HCID 67114960, compound

HRID 1408511Notes

Reaction equation

HRID 1408511 reaction equation
[C:1]1([N:7]2[C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:10][C:9]([C:16]([F:19])([F:18])[F:17])=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N+:20]([O-])([OH:22])=[O:21].OS(O)(=O)=O>C(O)(=O)C>[N+:20]([C:4]1[CH:3]=[CH:2][C:1]([N:7]2[C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:10][C:9]([C:16]([F:18])([F:19])[F:17])=[N:8]2)=[CH:6][CH:5]=1)([O-:22])=[O:21]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 12914838HCID 12914838, compound

Product 1

HCID 67114960HCID 67114960, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
0 °C

Procedure

Intermediate 8 (2 g, 7.4 mmol) was dissolved in acetic acid (15 ml), cooled to 0° C. and added nitration mixture (6 ml HNO3 and 6 ml H2SO4) drop-wise. Reaction mixture was heated to 60° C. for overnight. Work up (AcOEt:H2O) and purification on silicagel (60-120 mesh silicagel) using EA and pet ether (3:97) as eluent afforded the title compound (850 mg) as a white solid. 1H-NMR (δ ppm, CDCl3, 400 MHz): 8.37 (d, J 9, 2H), 7.68 (d, J 9, 2H), 7.31 (s, 1H), 3.87 (s, 3H).

Workup

  1. customReaction mixture
  2. temperaturewas heated to 60° C. for overnight
  3. custom(AcOEt:H2O) and purification on silicagel (60-120 mesh silicagel)

Sources & evidence

ORD record
ord-06351545162e40f9b132f2c2e58c4f5e
Source dataset
uspto-grants-2014_12
Patent number
US08921364B2

Reaction notes

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