N,N-Dimethylaniline → HCID 13286895, compound

HRID 1721434Notes

Reaction equation

HRID 1721434 reaction equation
C([O:4][C:5]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:6]=1[CH:7]=[C:8]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[NH:9]2)C=C.CN(C)[C:21]1[CH:26]=CC=C[CH:22]=1>CCCCCC>[CH2:26]([C:13]1[C:5]([OH:4])=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:7]2)[CH:21]=[CH2:22]

Participants

4

Reactant 2

HCID 949N,N-DimethylanilineHCID 13286892HCID 13286892, compound

Product 1

HCID 13286895HCID 13286895, compoundYield 50.2%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
200 °C

Procedure

2.79 g (11.4 mmol) of ethyl 4-allyloxyindole-2-carboxylate was added to 8.8 g of N,N-dimethylaniline, and the mixture was stirred for 15 minutes at 200° C. under a nitrogen atmosphere. 2.7 g of a crude product was obtained by adding n-hexane to the reaction mixture and collecting deposited crystals by filtration. This crude product was purified by column chromatography (silica gel, chloroform) to obtain 1.4 g (yield: 50.2%) of the target compound. This compound was recrystallized from a mixture of ethyl acetate and n-hexane to obtain colorless needles of the title compound.

Workup

  1. custom2.7 g of a crude product was obtained
  2. customcollecting
  3. filtrationby filtration
  4. customThis crude product was purified by column chromatography (silica gel, chloroform)

Sources & evidence

ORD record
ord-95af1fc8ce24461298b8d095a52dcc08
Source dataset
uspto-grants-1996_04
Patent number
US05510366

Reaction notes

Loading…