Ethyl Acetate → N-(3-amino-4-chloro-6-fluorophenyl)-3,4,5,6-tetrahydrophthalimide

HRID 363181

Reaktionsgleichung

Reaktionsgleichung von HRID 363181
[Cl:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][C:5]([N:11]2[C:20](=[O:21])[C:15]3[CH2:16][CH2:17][CH2:18][CH2:19][C:14]=3[C:12]2=[O:13])=[C:4]([F:22])[CH:3]=1.C(OCC)(=O)C>C(O)(=O)C.[Fe]>[NH2:8][C:7]1[C:2]([Cl:1])=[CH:3][C:4]([F:22])=[C:5]([N:11]2[C:20](=[O:21])[C:15]3[CH2:16][CH2:17][CH2:18][CH2:19][C:14]=3[C:12]2=[O:13])[CH:6]=1

Komponenten

5

Edukt 2

HCID 8857Ethyl AcetateHCID 15590179N-(4-chloro-2-fluoro-5-nitrophenyl)-3,4,5,6-tetrahydrophthalimide

Produkt 1

HCID 15590180N-(3-amino-4-chloro-6-fluorophenyl)-3,4,5,6-tetrahydrophthalimide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysatorHCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

Iron powder (7.30 g, 130.7 mmol) is added portionwise to a mixture. of N-(4-chloro-2-fluoro-5-nitrophenyl)-1-cyclohexene-1,2-dicarboximide (10.6 g, 32.7 mmol) in acetic acid (100 mL) at 65° C. After the addition is complete, the reaction mixture is stirred for 10 minutes, and filtered through diatomaceous earth. The filtrate is concentrated in vacuo to obtain a dark solid. A mixture of the solid in an ethyl acetate/saturated sodium hydrogen carbonate solution is filtered through diatomaceous earth, and the phases are separated. The organic phase is washed sequentially with saturated sodium hydrogen carbonate solution and brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo to give the title product as a yellow solid.

Aufarbeitung

  1. customat 65° C
  2. additionAfter the addition
  3. filtrationfiltered through diatomaceous earth
  4. concentrationThe filtrate is concentrated in vacuo
  5. customto obtain a dark solid
  6. filtrationis filtered through diatomaceous earth
  7. customthe phases are separated
  8. washThe organic phase is washed sequentially with saturated sodium hydrogen carbonate solution and brine
  9. dry with materialdried over anhydrous magnesium sulfate
  10. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-710856c0d8f143039e6fffccdcb45d12
Quelldatensatz
uspto-grants-1999_02
Patentnummer
US05872253

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