Benzene → 1-(3-Phenyl-2,3-dihydro-1H-indol-1-yl)prop-2-en-1-one

HRID 262293Notes

Reaction equation

HRID 262293 reaction equation
[C:1]1([CH:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[NH:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1C=CC=CC=1.[C:22](Cl)(=[O:25])[CH:23]=[CH2:24]>C(N(CC)CC)C>[C:22]([N:9]1[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:8]1)(=[O:25])[CH:23]=[CH2:24]

Participants

5

Reactant 3

HCID 241BenzeneHCID 13140Acryloyl chlorideHCID 109323533-phenyl-2,3-dihydro-1H-indole

Product 1

HCID 213204691-(3-Phenyl-2,3-dihydro-1H-indol-1-yl)prop-2-en-1-oneYield 45%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A mixture comprising 4.0 g of 3-phenylindoline, 40 ml of benzene, 5 ml of triethylamine and 4.0 g of acryloylchloride was stirred at 10°-15° C. for 15 minutes. The mixture was then washed with water, the benzene solution dried and the solvent removed. 4.1 G of resin which was crystallized from ether to give 2.3 g of the desired N-acryloyl-3-phenylindoline which was found to have a melting point of 77°-8° C.

Workup

  1. washThe mixture was then washed with water
  2. dry with materialthe benzene solution dried
  3. customthe solvent removed
  4. custom4.1 G of resin which was crystallized from ether

Sources & evidence

ORD record
ord-161bd1af8bcd43d681790fddd78f4396
Source dataset
uspto-grants-1979_05
Patent number
US04153789

Reaction notes

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