Hydrochloric Acid → HCID 22286045, compound

HRID 1672893Notes

Reaction equation

HRID 1672893 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-5ba27e1e946d4c349fa5196f83a978e8
Source dataset
uspto-grants-2011_08
Patent number
US07999006B2

Reaction notes

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