Triethylamine → 4-Fluoro-2-[(1-oxopropyl)amino]benzoic acid

HRID 2371443Notes

Reaction equation

HRID 2371443 reaction equation
[C:1](Cl)(=[O:4])[CH2:2][CH3:3].[F:6][C:7]1[CH:8]=[C:9]([NH2:16])[C:10](=[CH:14][CH:15]=1)[C:11]([OH:13])=[O:12].C(N(CC)CC)C>O1CCOCC1>[F:6][C:7]1[CH:8]=[C:9]([NH:16][C:1](=[O:4])[CH2:2][CH3:3])[C:10](=[CH:14][CH:15]=1)[C:11]([OH:13])=[O:12]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 27249674-Fluoroanthranilic acid

Product 1

HCID 167871954-Fluoro-2-[(1-oxopropyl)amino]benzoic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Propionyl chloride (1.7 ml) was added to a solution of 4-fluoroanthranilic acid (1 g) and triethylamine (2.8 ml) in 1,4-dioxane (30 ml). The mixture was heated under reflux for 4 hours, cooled and concentrated under reduced pressure. The residue was suspended in ethyl acetate and extracted with water. The organic phase was dried and evaporated and the residue purified by silica gel chromatography to give 4-fluoro-N-propionylanthranilic acid, mp 170°-171°. (Compound 9).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 4 hours
  3. temperaturecooled
  4. concentrationconcentrated under reduced pressure
  5. extractionextracted with water
  6. customThe organic phase was dried
  7. customevaporated
  8. customthe residue purified by silica gel chromatography

Sources & evidence

ORD record
ord-c2d1eb11bc534865acec2db3d6c493a4
Source dataset
uspto-grants-1992_03
Patent number
US05093364

Reaction notes

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