Nitric Acid → HCID 86745637, compound

HRID 1029520Notes

Reaction equation

HRID 1029520 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 for 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 a eluent gives a solid. Recrystallization from hexanes gives the title compound as a white solid (2.02 g, 55%), mp 90° C.-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-eef786571edd4053bbadd27de355d77b
Source dataset
uspto-grants-1992_04
Patent number
US05102904

Reaction notes

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