3,4,5,6-Tetrahydrophthalic anhydride → HCID 14129444, compound

HRID 1722917Notes

Reaction equation

HRID 1722917 reaction equation
[Cl:1][C:2]1[C:8]([O:9][CH2:10][CH:11]2[CH2:13][C:12]2([Cl:15])[Cl:14])=[CH:7][C:5]([NH2:6])=[C:4]([F:16])[CH:3]=1.[C:17]1(=O)[O:22][C:20](=[O:21])[C:19]2[CH2:23][CH2:24][CH2:25][CH2:26][C:18]1=2>C(O)(=O)C>[Cl:1][C:2]1[C:8]([O:9][CH2:10][CH:11]2[CH2:13][C:12]2([Cl:14])[Cl:15])=[CH:7][C:5]([N:6]2[C:20](=[O:21])[C:19]3[CH2:23][CH2:24][CH2:25][CH2:26][C:18]=3[C:17]2=[O:22])=[C:4]([F:16])[CH:3]=1

Participants

4

Reactant 2

HCID 124753,4,5,6-Tetrahydrophthalic anhydrideHCID 54151533HCID 54151533, compound

Product 1

HCID 14129444HCID 14129444, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

8.9 g (0.031 mol) 4-Chloro-2-fluoro-5-(2,2-dichlorocyclopropylmethoxy) aniline was dissolved in 12.5 ml acetic acid and 3.85 g 3,4,5,6-tetrahydrophthalic anhydride added. The mixture was heated under reflux for 3 hours, then poured into ice-water and extracted with ether. The ether phase was neutralised with aqueous sodium hydrogen carbonate, washed with saturated brine, dried over magnesium sulphate and the solvent removed. The residue was chromatographed on silica gel using a mixture of 9 parts hexane and 1 part ethyl acetate as eluent.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 3 hours
  3. extractionextracted with ether
  4. washwashed with saturated brine
  5. dry with materialdried over magnesium sulphate
  6. customthe solvent removed
  7. customThe residue was chromatographed on silica gel using
  8. additiona mixture of 9 parts hexane and 1 part ethyl acetate as eluent

Sources & evidence

ORD record
ord-8131452b160c4816a091d01700a120eb
Source dataset
uspto-grants-1989_08
Patent number
US04859230

Reaction notes

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