Tetrahydrofuran → 4-Phenylindolin-2-one

HRID 652260

Reaction equation

HRID 652260 reaction equation
[C:1]1([C:7]2[CH:15]=[CH:14][CH:13]=[C:12]3[C:8]=2[CH:9](SC)[C:10](=[O:16])[NH:11]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O1CCCC1>[Ni].O.C(O)(C)C>[C:1]1([C:7]2[CH:15]=[CH:14][CH:13]=[C:12]3[C:8]=2[CH2:9][C:10](=[O:16])[NH:11]3)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 129098184-Phenyl-3-methylthioindolin-2-one

Product 1

HCID 130486014-Phenylindolin-2-one

Reagents, catalysts & solvents 2

HCID 444642Hydroxy-nickelCatalystHCID 3776IsopropanolSolvent

Procedure

A stirring solution of 3.5 g. (0.014 mole) of 4-phenyl-3-methylthioindolin-2-one in 75 ml. of tetrahydrofuran was treated portionwise with 20 g. of a commercial Raney nickel/water suspension. The mixture was filtered through Celite and the filtrate was concentrated to give a yellow solid. The solid was recrystallized to give a yellow solid. This solid was recrystallized from benzene to yield 1.6 g. (57%) of product as an off-white solid. An analytical sample was prepared from isopropanol; m.p. 192°-194° C.

Workup

  1. filtrationThe mixture was filtered through Celite
  2. concentrationthe filtrate was concentrated
  3. customto give a yellow solid
  4. customThe solid was recrystallized
  5. customto give a yellow solid
  6. customThis solid was recrystallized from benzene
  7. customto yield 1.6 g

Sources & evidence

ORD record
ord-cf1af035e0954f63bc874828617deefe
Source dataset
uspto-grants-1987_06
Patent number
US04670566

Linked notes

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