Aniline → HCID 136333568, compound

HRID 1081967Notes

Reaction equation

HRID 1081967 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[CH:11]=O)=[CH:8][CH:7]=[CH:6][CH:5]=2.CCCCCC.[NH2:19]C1C=CC=CC=1>C1(C)C=CC=CC=1>[CH3:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[CH:11]=[NH:19])=[CH:8][CH:7]=[CH:6][CH:5]=2

Participants

5

Reactant 3

HCID 6115AnilineHCID 8058HexaneHCID 731663-Formyl-2-methylindole

Product 1

HCID 136333568HCID 136333568, compoundYield 110.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
70 °C

Procedure

2-methylindole-3-carboxaldehyde (10 g, 0.06 mol) was mixed with hexane (40 ml), to which aniline (9.6 ml, 0.11 mol) was added and stirred at 70° C. for 3.5 hours under reflux. Then, toluene (20 ml) was added and dissolved. The mixture was then submitted to silica gel column chromatography. The column was eluted by a developing solvent of hexane/ethyl acetate=3/1 and a fraction containing the desired product was concentrated by distilling off the solvent, to obtain 10.5 g (yield: 75%) of 2-methylindole-3-carboxaldehyde imine. 1H-NMR spectra (chemical shift, ppm: in CDCl3): 2.63 (3H, s), 7.15-7.42 (8H, m), 8.19 (1H, s), 8.45-8.48 (1H, m), 8.69 (1H, s).

Workup

  1. additionwas added
  2. temperatureunder reflux
  3. dissolutiondissolved
  4. washThe column was eluted by a developing solvent of hexane/ethyl acetate=3/1
  5. additiona fraction containing the desired product
  6. concentrationwas concentrated
  7. distillationby distilling off the solvent

Sources & evidence

ORD record
ord-08168e74db3a45afb88c2a401e76049f
Source dataset
uspto-grants-1996_12
Patent number
US05587486

Reaction notes

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