Hydrochloric Acid → HCID 615848, compound

HRID 1596095Notes

Reaction equation

HRID 1596095 reaction equation
[NH2:1][C:2]1[C:10]([F:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].C(=O)([O-])[O-].[K+].[K+].[F:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1I.Cl>C1(O)CCCCC1.[Cu]>[F:11][C:10]1[C:2]([NH:1][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[F:18])=[C:3]([CH:7]=[CH:8][CH:9]=1)[C:4]([OH:6])=[O:5]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 676731-Fluoro-2-iodobenzeneHCID 5864082-Amino-3-fluorobenzoic acid

Product 1

HCID 615848HCID 615848, compoundYield 71.2%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 7966CyclohexanolSolvent

Procedure

A mixture of 14.0 g (90.2 mmol) of 2-amino-3-fluorobenzoic acid (XIV), 12.5 g (90.4 mmol) of potassium carbonate, 21.0 g (94.6 mmol) of 2-fluoroiodobenzene (XV) and a spatula-tipfull of copper powder in 85 ml of cyclohexanol was heated at reflux for 12 hours. The solvent was then removed by steam distillation, and the aqueous residue obtained was subjected to centrifugation. The soluble centrifugate was acidified with diluted hydrochloric acid, and the resulting precipitate was filtered off and dried. Fractional sublimation of the solid under high vacuum yielded 16.0 g (71% of theory) of 3-fluoro-2-(2-fluorophenylamino)benzoic acid (XVI) as a yellow powder with a melting point of 176° C.

Workup

  1. temperatureat reflux for 12 hours
  2. customThe solvent was then removed by steam distillation
  3. customthe aqueous residue obtained
  4. filtrationthe resulting precipitate was filtered off
  5. customdried

Sources & evidence

ORD record
ord-facca918977045a789fd878d4f5e4265
Source dataset
uspto-grants-2001_09
Patent number
US06290926B1

Reaction notes

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