N-Ethylaniline → HCID 524499, compound

HRID 1911949Notes

Reaction equation

HRID 1911949 reaction equation
Cl[CH:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C:3]1=O.[CH2:9]([NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH3:10].COCCO.C(=O)([O-])[O-].[Na+].[Na+]>O.N1C=CC=CC=1>[CH2:9]([N:11]1[C:12]2[CH2:17][CH2:16][CH2:15][CH2:14][C:13]=2[C:3]2[C:2]1=[CH:7][CH:6]=[CH:5][CH:4]=2)[CH3:10]

Participants

7

Reactant 4

HCID 7670N-EthylanilineHCID 80192-MethoxyethanolHCID 10340Sodium CarbonateHCID 132032-Chlorocyclohexanone

Product 1

HCID 524499HCID 524499, compoundYield 24.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Conditions

Temperature
100 °C

Procedure

132.5 g of 2-chloro-cyclohexanone was added to 123.42 g of N-ethyl aniline, 500 ml of methyl cellosolve, 127 g of dry sodium carbonate and 7.9 g of pyridine at 30-40° C. over a period of 1 hour. Reaction mass was heated to 100° C. and stirred for 2 hours. Reaction temperature was further raised to 130° C. and held at this temperature till no more water get distilled. Reaction mass was then worked up to get 48.2 g of crude 9-ethyl-tetrahydrocarbazole of 96.3% GC purity.

Workup

  1. customReaction mass
  2. customReaction temperature
  3. temperaturewas further raised to 130° C.
  4. customget
  5. distillationdistilled
  6. customReaction mass

Sources & evidence

ORD record
ord-50d9e8810bc24b3ba7e7a2ea1bc38fde
Source dataset
uspto-grants-2013_12
Patent number
US08604219B2

Reaction notes

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