HCID 20446192, compound → HCID 20446293, compound

HRID 2418390Notes

Reaction equation

HRID 2418390 reaction equation
[O:1]=[C:2]1[CH:10](SC)[C:9]2[C:4](=[C:5]([Cl:20])[CH:6]=[CH:7][C:8]=2[O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[NH:3]1>[Ni].O1CCOCC1>[O:1]=[C:2]1[CH2:10][C:9]2[C:4](=[C:5]([Cl:20])[CH:6]=[CH:7][C:8]=2[O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[NH:3]1

Participants

4

Reactant 1

HCID 20446192HCID 20446192, compound

Product 1

HCID 20446293HCID 20446293, compoundYield 84.4%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
70 °C

Procedure

2-Oxo-3-methylthio-4-phenoxy-7-chloroindoline (6 g) was added to a mixture of Raney nickel (15 ml) and dioxane (80 ml), and the mixture was stirred at 70° C. for 2 hours. The reaction mixture was allowed to stand at room temperature, and the supernatant was separated by decantation. To the residue was added dioxane (50 ml), and the supernatant was separated again. The dioxane solution was combined and filtered. The filtrate was evaporated in vacuo, and the residue was washed with diethyl ether and dried to give 2-oxo-4-phenoxy-7-chloroindoline (4.3 g). mp. 200°-202° C.

Workup

  1. customto stand at room temperature
  2. customthe supernatant was separated by decantation
  3. additionTo the residue was added dioxane (50 ml)
  4. customthe supernatant was separated again
  5. filtrationfiltered
  6. customThe filtrate was evaporated in vacuo
  7. washthe residue was washed with diethyl ether
  8. customdried

Sources & evidence

ORD record
ord-64cb0b32790b4c15a4418b847aa168d5
Source dataset
uspto-grants-1984_09
Patent number
US04472433

Reaction notes

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