Acetic Acid → N-[4-chloro-2-fluoro-5-(1-methoxyethyl)phenyl]-3,4,5,6-tetrahydrophthalimide

HRID 231427Notes

Reaction equation

HRID 231427 reaction equation
[Cl:1][C:2]1[C:8]([CH:9]([O:11][CH3:12])[CH3:10])=[CH:7][C:5]([NH2:6])=[C:4]([F:13])[CH:3]=1.[C:14]1(=O)[O:19][C:17](=[O:18])[CH:16]2[CH2:20][CH2:21][CH:22]=[CH:23][CH:15]12.C(O)(=O)C>C(OCC)C>[Cl:1][C:2]1[C:8]([CH:9]([O:11][CH3:12])[CH3:10])=[CH:7][C:5]([N:6]2[C:17](=[O:18])[C:16]3[CH2:20][CH2:21][CH2:22][CH2:23][C:15]=3[C:14]2=[O:19])=[C:4]([F:13])[CH:3]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 127266013a,4,5,7a-Tetrahydro-2-benzofuran-1,3-dioneHCID 14501809HCID 14501809, compound

Product 1

HCID 20032354N-[4-chloro-2-fluoro-5-(1-methoxyethyl)phenyl]-3,4,5,6-tetrahydrophthalimideYield 40.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 0.58 g (0.0029 mole) of 4-chloro-2-fluoro-5-(1-methoxyethyl)aniline, 0.82 g (0.0054 mole) of tetrahydrophthalic anhydride, and 15 ml of acetic acid was refluxed overnight. The acetic acid was then evaporated under reduced pressure, leaving a residue which was dissolved in diethyl ether. This solution was washed successively with water and an aqueous solution of sodium bicarbonate. The solution was dried, filtered, and the solvent was evaporated under reduced pressure leaving a residue. This residue was passed through a silica gel column, eluting with ethyl acetate/heptane (1/4). Appropriate fractions were combined, and the solvent was evaporated under reduced pressure, yielding 0.4 g of N-[4-chloro-2-fluoro-5-(1-methoxyethyl)phenyl]-3,4,5,6-tetrahydrophthalimide as a solid, m.p. 141°-44° C. The nmr and ir spectra were consistent with the proposed structure.

Workup

  1. temperaturewas refluxed overnight
  2. customThe acetic acid was then evaporated under reduced pressure
  3. customleaving a residue which
  4. washThis solution was washed successively with water
  5. customThe solution was dried
  6. filtrationfiltered
  7. customthe solvent was evaporated under reduced pressure
  8. customleaving a residue
  9. washeluting with ethyl acetate/heptane (1/4)
  10. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-4c216e5b822b4668ab93fedf00ba693d
Source dataset
uspto-grants-1989_07
Patent number
US04846882

Reaction notes

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