3,4,5,6-Tetrahydrophthalic anhydride → N-(2-fluoro-5-hydroxyphenyl)-3,4,5,6-tetrahydrophthalimide

HRID 1284612Notes

Reaction equation

HRID 1284612 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=1[F:8].[C:10]1(=O)[O:15][C:13](=[O:14])[C:12]2[CH2:16][CH2:17][CH2:18][CH2:19][C:11]1=2>C(O)(=O)C>[F:8][C:7]1[CH:6]=[CH:5][C:4]([OH:9])=[CH:3][C:2]=1[N:1]1[C:13](=[O:14])[C:12]2[CH2:16][CH2:17][CH2:18][CH2:19][C:11]=2[C:10]1=[O:15]

Participants

4

Reactant 2

HCID 124753,4,5,6-Tetrahydrophthalic anhydrideHCID 135191803-Amino-4-fluorophenol

Product 1

HCID 13519181N-(2-fluoro-5-hydroxyphenyl)-3,4,5,6-tetrahydrophthalimideYield 80.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

3-Amino-4-fluorophenol (V) (2 g) and 3,4,5,6-tetrahydrophthalic anhydride (2.4 g) were dissolved in acetic acid (50 ml), and the resultant solution was heated under reflux for lhour, followed by extraction with ethyl acetate. The extract was concentrated, and the precipitated crystals were collected by filtration and washed with a small amount of ether to give 3.3 g of N-(2-fluoro-5-hydroxyphenyl)-3,4,5,6-tetrahydrophthalimide (VI). M.P. 164.6° C.

Workup

  1. temperatureunder reflux for lhour
  2. extractionfollowed by extraction with ethyl acetate
  3. concentrationThe extract was concentrated
  4. filtrationthe precipitated crystals were collected by filtration
  5. washwashed with a small amount of ether

Sources & evidence

ORD record
ord-571c527e43824ffeb59bcefbc6624c33
Source dataset
uspto-grants-1986_01
Patent number
US04563535

Reaction notes

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