N,N-Diethylaniline → HCID 22238067, compound

HRID 1743391Notes

Reaction equation

HRID 1743391 reaction equation
[CH3:1][C:2]1[C:10]([CH3:11])=[C:9]2[C:5]([CH2:6][CH2:7][N:8]2[CH:12]=[O:13])=[CH:4][C:3]=1[O:14]CC(C)=C.C(O[CH:23]([CH3:25])[CH3:24])(C)C.[CH2:26](N(CC)C1C=CC=CC=1)C>>[OH:14][C:3]1[C:4]([CH2:24][C:23]([CH3:25])=[CH2:26])=[C:5]2[C:9](=[C:10]([CH3:11])[C:2]=1[CH3:1])[N:8]([CH:12]=[O:13])[CH2:7][CH2:6]2

Participants

4

Reactant 3

HCID 7061N,N-DiethylanilineHCID 7914Diisopropyl EtherHCID 22238069HCID 22238069, compound

Product 1

HCID 22238067HCID 22238067, compoundYield 81%

Procedure

A solution of 2,3-dihydro-6,7-dimethyl-5-[(2-methyl-2-propenyl)oxy]-1H-indole-1-carbaldehyde (25.2 g, 0.103 mol) in N,N-diethylaniline (50 mL) was stirred at 200° C. for 8 hours under the nitrogen atmosphere. The reaction mixture was allowed to stand overnight, diisopropyl ether was added, the crystals were filtered, and recrystallized from ethanol to obtain 20.4 g of the title compound.

Workup

  1. filtrationthe crystals were filtered
  2. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-6a931ef67c0b4e37aa3c1d1d1fc0b996
Source dataset
uspto-grants-2006_03
Patent number
US07008940B1

Reaction notes

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