Hydrochloric Acid → 6-Phenyl-1,3-dihydro-indol-2-one

HRID 652261Notes

Reaction equation

HRID 652261 reaction equation
CS[CH:3]1[C:11]2[C:6](=[CH:7][C:8]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[CH:9][CH:10]=2)[NH:5][C:4]1=[O:18].[Sn].Cl>C(O)C>[C:12]1([C:8]2[CH:7]=[C:6]3[C:11]([CH2:3][C:4](=[O:18])[NH:5]3)=[CH:10][CH:9]=2)[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 5352426Tin atomHCID 12909819HCID 12909819, compound

Product 1

HCID 105363846-Phenyl-1,3-dihydro-indol-2-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3.5 g. (0.014 mole) of 3-methylthio-6-phenylindolin-2-one, 7 g. of tin, 10 ml. of concentrated hydrochloric acid and 50 ml. of ethanol was refluxed 4 hours under nitrogen. The hot mixture was filtered and the filtrate concentrated to give a tan solid. The solid was further purified by vacuum sublimation at 0.01 mm. and 200° C. and then crystallized from benzene to give 0.5 g. (17%) of product as a white solid which melted at 173°-175° C.

Workup

  1. additionA mixture of 3.5 g
  2. filtrationThe hot mixture was filtered
  3. concentrationthe filtrate concentrated
  4. customto give a tan solid
  5. customThe solid was further purified by vacuum sublimation at 0.01 mm
  6. customand 200° C. and then crystallized from benzene
  7. customto give 0.5 g

Sources & evidence

ORD record
ord-cccf1a282f784ed997a41275a48bbab8
Source dataset
uspto-grants-1987_06
Patent number
US04670566

Reaction notes

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