HCID 21925692, compound → HCID 21925676, compound

HRID 1700245Notes

Reaction equation

HRID 1700245 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[CH:23](C(OC)=O)[C:24]([O:26]C)=[O:25])([O-:3])=[O:2]>Cl>[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:19])([F:20])[F:21])[CH:11]=2)[CH:7]=[CH:6][C:5]=1[CH2:23][C:24]([OH:26])=[O:25])([O-:3])=[O:2]

Participants

3

Reactant 1

HCID 21925692HCID 21925692, compound

Product 1

HCID 21925676HCID 21925676, compoundYield 73.4%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Dimethyl 2-[2-nitro-4-(3-trifluoroacetamidophenyl)phenyl]-malonate (4.4 g) was refluxed overnight in 50 mL 6N hydrochloric acid. The reaction mixture was cooled to room temperature and the solids were collected by vacuum filtration, washed with water, and dried under vacuum to give 2.7 g (73% yield) of 2-[2-nitro-4-(3-trifluoroacetamidophenyl)phenyl]acetic acid. 2-[2-Nitro-4-(3-trifluoroacetamidophenyl)phenyl]acetic acid (100 mg) and 50 mg iron powder in 3 mL acetic acid was heated at 100° C. for 2 hours. The reaction mixture was concentrated and the residue sonicated in 5 mL ethyl acetate. The insoluble solids were removed by vacuum filtration and the filtrate washed with 1N 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. filtrationthe solids were collected by vacuum filtration
  2. washwashed with water
  3. customdried under vacuum

Sources & evidence

ORD record
ord-79a3f6c822c04e51a026d60cab281e98
Source dataset
uspto-grants-2002_02
Patent number
US06350754B2

Reaction notes

Loading…