2-Fluorobenzoyl chloride → HCID 54292599, compound

HRID 355685Notes

Reaction equation

HRID 355685 reaction equation
[NH2:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[OH:11].[F:12][C:13]1[CH:21]=[CH:20][CH:19]=[CH:18][C:14]=1[C:15](Cl)=[O:16]>N1C=CC=CC=1>[F:12][C:13]1[CH:21]=[CH:20][CH:19]=[CH:18][C:14]=1[C:15]([NH:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[OH:11])=[O:16]

Participants

4

Reactant 2

HCID 98082-Fluorobenzoyl chlorideHCID 41154952-Amino-3-Nitrophenol

Product 1

HCID 54292599HCID 54292599, compoundYield 85.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

1.57 g (10 mmol) of 2-amino-3-nitrophenol was dissolved in 20 ml of pyridine and 3.36 g (21 mmol) of 2-fluorobenzoyl chloride was added thereto under stirring. After heating under reflux for 4 hours, the mixture was concentrated. Then dilute hydrochloric acid and ethyl acetate were added thereto. The organic layer was separated and washed with water. After concentrating, 20 ml of tetrahydrofuran and 20 ml of 1N sodium hydroxide were added and the mixture was heated under reflux for 4 hours. After cooling, it was neutralized with hydrochloric acid and concentrated. After adding ethyl acetate and water, the organic layer was separated, washed with water and dried over magnesium sulfate. After concentrating, the residue was purified by silica gel column chromatography. Thus 2.35 g of 2-fluoro-N-(2-hydroxy-6-nitrophenyl)benzamide was obtained. 553 mg (2 mmol) of this powder was dissolved in 20 ml of dimethylformamide and 332 mg (2.4 mmol) of potassium carbonate and 20 mg of a copper powder were added thereto. After heating under reflux for 3 hours and concentrating, ethyl acetate and dilute hydrochloric acid were added to the residue. The formed insoluble matters were filtered off and the organic layer was separated, washed with water, dried over magnesium sulfate and concentrated. Then the residue was purified by silica gel column chromatography. Thus 400 mg of the title compound was obtained.

Workup

  1. temperatureAfter heating
  2. temperatureunder reflux for 4 hours
  3. concentrationthe mixture was concentrated
  4. additionThen dilute hydrochloric acid and ethyl acetate were added
  5. customThe organic layer was separated
  6. washwashed with water
  7. concentrationAfter concentrating
  8. addition20 ml of tetrahydrofuran and 20 ml of 1N sodium hydroxide were added
  9. temperaturethe mixture was heated
  10. temperatureunder reflux for 4 hours
  11. temperatureAfter cooling
  12. concentrationconcentrated
  13. additionAfter adding ethyl acetate and water
  14. customthe organic layer was separated
  15. washwashed with water
  16. dry with materialdried over magnesium sulfate
  17. concentrationAfter concentrating
  18. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-e7ab4743f61f40c4aab7d4ff2e6f6c1a
Source dataset
uspto-grants-1998_11
Patent number
US05834462

Reaction notes

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