HCID 53925309, compound → HCID 20446208, compound

HRID 2418379Notes

Reaction equation

HRID 2418379 reaction equation
[O:1]=[C:2]1[CH:10](SC)[C:9]2[C:4](=[C:5]([O:13][C:14]3[C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[CH:17]=[CH:16][CH:15]=3)[CH:6]=[CH:7][CH:8]=2)[NH:3]1>[Ni].O1CCOCC1>[O:1]=[C:2]1[CH2:10][C:9]2[C:4](=[C:5]([O:13][C:14]3[C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[CH:17]=[CH:16][CH:15]=3)[CH:6]=[CH:7][CH:8]=2)[NH:3]1

Participants

4

Reactant 1

HCID 53925309HCID 53925309, compound

Product 1

HCID 20446208HCID 20446208, compoundYield 68.1%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 2-oxo-3-methylthio-7-(α-naphthoxy)indoline (5.4 g) and Raney nickel (12 ml) in dioxane (70 ml) was stirred at 50° C. for 1.5 hrs. The reaction mixture was allowed to stand and the supernatant was separated by decantation. To the residue was added dioxane and the supernatant was separated again. The dioxane solutions were combined and filtered. The filtrate was evaporated in vacuo, and the oily residue (5.2 g) was crystallized by treating with ethanol to give 2-oxo-7-(α-naphtoxy)indoline (3.15 g). mp 158°-160° C.

Workup

  1. customthe supernatant was separated by decantation
  2. additionTo the residue was added dioxane
  3. customthe supernatant was separated again
  4. filtrationfiltered
  5. customThe filtrate was evaporated in vacuo
  6. customthe oily residue (5.2 g) was crystallized
  7. additionby treating with ethanol

Sources & evidence

ORD record
ord-bdd7e28f3f494ccaa483f5f091eb7fb4
Source dataset
uspto-grants-1984_09
Patent number
US04472433

Reaction notes

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