Hydrochloric Acid → HCID 22286045, compound

HRID 1717551Notes

Reaction equation

HRID 1717551 reaction equation
F[C:2]1[CH:10]=[C:9]([F:11])[C:8]([F:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[F:13][C:14]1[CH:20]=[C:19]([I:21])[CH:18]=[CH:17][C:15]=1[NH2:16].[NH2-].[Li+].Cl>C(#N)C>[F:11][C:9]1[C:8]([F:12])=[CH:7][C:3]([C:4]([OH:6])=[O:5])=[C:2]([NH:16][C:15]2[CH:17]=[CH:18][C:19]([I:21])=[CH:20][C:14]=2[F:13])[CH:10]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24532Lithium amideHCID 1856942-Fluoro-4-iodoanilineHCID 5211702,4,5-Trifluorobenzoic acid

Product 1

HCID 22286045HCID 22286045, compoundYield 43.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

2,4,5-Trifluorobenzoic acid (643 mg, 3.65 mmol) and 2-fluoro-4-iodoaniline (1.0 g, 4.22 mmol) were taken into acetonitrile (30 mL) followed by addition of lithium amide (290 mg, 12.7 mmol) and the mixture was heated to 60° C. under a nitrogen atmosphere for one hour. On cooling to room temperature the mixture was added to 1 N aqueous hydrochloric acid (100 mL) and the precipitate formed was collected by filtration and washed once with water then hexanes and dried in vacuo to give 4,5-difluoro-2-[(2-fluoro-4-iodophenyl)amino]benzoic acid (624 mg, 43% yield) as a tan solid. 1H-NMR (400 MHz, D6-DMSO): 13.65 (br s, 1H), 9.63 (s, 1H), 7.84 (tr, 1H), 7.71 (d, 1H), 7.52 (d, 1H), 7.32 (tr, 1H), 7.03-6.98 (dd, 1H).

Workup

  1. temperatureOn cooling to room temperature the mixture
  2. customthe precipitate formed
  3. filtrationwas collected by filtration
  4. washwashed once with water
  5. dry with materialhexanes and dried in vacuo

Sources & evidence

ORD record
ord-34ccfa15fc6a49e4976767bc8b2621f4
Source dataset
uspto-grants-2010_09
Patent number
US07803839B2

Reaction notes

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