Ethyl Acetate → 5-Fluoro-1-(4-fluorophenyl)indoline-2,3-dione

HRID 1638479Notes

Reaction equation

HRID 1638479 reaction equation
[C:1](Cl)(=[O:5])[C:2](Cl)=[O:3].[F:7][C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)=[CH:10][CH:9]=1.[Al+3].[Cl-].[Cl-].[Cl-].C(OCC)(=O)C>C(Cl)Cl.O>[F:7][C:8]1[CH:9]=[CH:10][C:11]([N:14]2[C:15]3[C:16](=[CH:17][C:18]([F:21])=[CH:19][CH:20]=3)[C:1](=[O:5])[C:2]2=[O:3])=[CH:12][CH:13]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 65578Oxalyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 112411734-Fluoro-N-(4-fluorophenyl)benzenamine

Product 1

HCID 133395515-Fluoro-1-(4-fluorophenyl)indoline-2,3-dione

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

Oxalyl chloride (9.62 ml, 0.11 mole) was dissolved in 45 ml CH2Cl2. A solution of di-(4-fluorophenyl)amine (19.7 g, 0.096 mole) in 145 ml CH2Cl2 was added over 15 minutes; the temperature rose from 23° to 28°. After stirring 1 hour, AlCl3 (40.8 g) was added portionwise over 15 minutes; the temperature rose from 20° to 30°, and was kept less than 30° by cooling. After stirring for 10 minutes, the reaction mixture was added to 250 ml ethyl acetate and 500 ml ice and water (the temperature rose to 30° C.). The aqueous layer was washed 2×250 ml ethyl acetate. The organic layers were combined, back-washed 1×400 ml H2O, dried over MgSO4, evaporated to solids and triturated with 100 ml 1:1 ether:hexane to recover title product, 19.9 g, m.p. 180°-190°, tlc Rf 0.55 (1:1 ether:hexane).

Workup

  1. customrose from 23° to 28°
  2. customrose from 20° to 30°
  3. customwas kept less than 30°
  4. temperatureby cooling
  5. stirringAfter stirring for 10 minutes
  6. customrose to 30° C.
  7. washThe aqueous layer was washed 2×250 ml ethyl acetate
  8. washback-washed 1×400 ml H2O
  9. dry with materialdried over MgSO4
  10. customevaporated to solids
  11. customtriturated with 100 ml 1:1 ether
  12. customhexane to recover title product, 19.9 g, m.p. 180°-190°, tlc Rf 0.55 (1:1 ether:hexane)

Sources & evidence

ORD record
ord-7ea17133a33e46c2b2dc1c2bd348e335
Source dataset
uspto-grants-1989_11
Patent number
US04879391

Reaction notes

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