HCID 21925676, compound → HCID 23559333, compound

HRID 1057466Notes

Reaction equation

HRID 1057466 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([NH:16][C:17](=[O:22])[C:18]([F:21])([F:20])[F:19])[CH:11]=2)[CH:7]=[CH:6][C:5]=1[CH2:23][C:24](O)=[O:25])([O-])=O>C(O)(=O)C.[Fe]>[F:19][C:18]([F:21])([F:20])[C:17]([NH:16][C:12]1[CH:11]=[C:10]([C:8]2[CH:9]=[C:4]3[C:5]([CH2:23][C:24](=[O:25])[NH:1]3)=[CH:6][CH:7]=2)[CH:15]=[CH:14][CH:13]=1)=[O:22]

Participants

4

Reactant 1

HCID 21925676HCID 21925676, compound

Product 1

HCID 23559333HCID 23559333, compoundYield 14%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

2-[2-Nitro-4-(3-trifluoroacetamidophenyl)phenyl]acetic acid (100 mg) and 50 mg of iron powder in 3 mL of acetic acid was heated to 100° C. for 2 hours. The reaction mixture was concentrated and the residue sonicated in 5 mL of ethyl acetate. The insoluble solids were removed by vacuum filtration and the filtrate washed with 1 N hydrochloric acid, water and brine, dried over anhydrous sodium sulfate and concentrated to give 10 mg (14% yield) of the title compound as a rose-colored solid.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue sonicated in 5 mL of ethyl acetate
  3. customThe insoluble solids were removed by vacuum filtration
  4. washthe filtrate washed with 1 N hydrochloric acid, water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-514c0d4dfee84f949333402b3015bea7
Source dataset
uspto-grants-2003_02
Patent number
US06514981B1

Reaction notes

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