Water → HCID 18519624, compound

HRID 277411Notes

Reaction equation

HRID 277411 reaction equation
[NH2:1][C:2]1[C:3]([F:10])=[CH:4][C:5]([Cl:9])=[C:6]([OH:8])[CH:7]=1.[C:11]1(=O)[O:16][C:14](=[O:15])[C:13]2=[CH:17][CH:18]=[CH:19][CH:20]=[C:12]12.O>C(O)(=O)C>[Cl:9][C:5]1[CH:4]=[C:3]([F:10])[C:2]([N:1]2[C:14](=[O:15])[C:13]3=[CH:17][CH:18]=[CH:19][CH:20]=[C:12]3[C:11]2=[O:16])=[CH:7][C:6]=1[OH:8]

Participants

5

Reactant 3

HCID 962WaterHCID 6811Phthalic AnhydrideHCID 1586545-Amino-2-chloro-4-fluorophenol

Product 1

HCID 18519624HCID 18519624, compoundYield 92.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

5-Amino-2-chloro-4-fluorophenol (3.0 g, 18.6 mmol) and phthalic anhydride (3.3 g, 22.3 mmol) were dissolved in glacial acetic acid (60 ml) and the solution refluxed for 2 hr. Water was added and the resultant precipitate was separated by filtration. The residue was washed with water and dried to afford the title compound (5.04 g); 1H NMR (CDCl3+CD3OD, 300 MHz) 3.68 (1H, s), 6.93 (1H, d, J=6.6 Hz), 7.27 (1H, d, J=9.1 Hz), 7.84 (2H, dd, J=3.0, 5.5 Hz), dd, J=3.0, 5.5 Hz) ppm.

Workup

  1. temperaturethe solution refluxed for 2 hr
  2. customthe resultant precipitate was separated by filtration
  3. washThe residue was washed with water
  4. customdried

Sources & evidence

ORD record
ord-07d3adfb06de4c8091035dadb5af65bc
Source dataset
uspto-grants-2002_03
Patent number
US06355799B1

Reaction notes

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