Nitric Acid → HCID 86745637, compound

HRID 2253803Notes

Reaction equation

HRID 2253803 reaction equation
[N+:1]([O-:4])(O)=[O:2].[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[N:16]([O:17][CH3:18])[C:15]([C:19]([F:22])([F:21])[F:20])=[C:14]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:13]=2)=[CH:8][CH:7]=1>C(OC(=O)C)(=O)C.O.C(Cl)Cl.C(OCC)(=O)C>[Cl:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]2[N:16]([O:17][CH3:18])[C:15]([C:19]([F:21])([F:22])[F:20])=[C:14]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[C:13]=2[N+:1]([O-:4])=[O:2])=[CH:10][CH:11]=1

Participants

7

Reactant 2

HCID 944Nitric AcidHCID 86745638HCID 86745638, compound

Product 1

HCID 86745637HCID 86745637, compoundYield 55%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×HCID 7918Acetic AnhydrideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Fuming nitric acid (90%, 0.75 mL, 0.0167 mol) is added dropwise to a 5° C. solution of 5-(p-chlorophenyl)-1-methoxy-2-(trifluoromethyl)pyrrole-3-carboxylic acid, ethyl ester (3.27 g, 0.0094 mol) in acetic anhydride. After stirring at room temperature overnight, the reaction mixture is diluted with water and extracted with ether. The combined ether extracts are washed sequentially with water and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to give a thick yellow liquid. Chromatography using silica gel, methylene chloride and 2% ethyl acetate in methylene chloride as eluent gives a solid. Recrystallization from hexanes gives the title compound as a white solid (2.02 g, 55%), mp 90°-92° C.

Workup

  1. extractionextracted with ether
  2. washThe combined ether extracts are washed sequentially with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customto give a thick yellow liquid
  6. customgives a solid
  7. customRecrystallization from hexanes

Sources & evidence

ORD record
ord-9f7444832ccf40fca5425196fcaf5e0f
Source dataset
uspto-grants-1993_08
Patent number
US05232979

Reaction notes

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