N,N-Dimethylaniline → 6-Methoxy-2-(4-methoxyphenyl)-1H-indole

HRID 1719869Notes

Reaction equation

HRID 1719869 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([NH2:9])[CH:4]=1.CN(C)C1C=CC=CC=1.[C:19]([O:22][CH2:23][CH3:24])(=O)C.[C:25]1([CH3:32])[C:26](C)=[CH:27]C=[CH:29][CH:30]=1>>[CH3:19][O:22][C:23]1[CH:24]=[CH:32][C:25]([C:26]2[NH:9][C:5]3[C:6]([CH:27]=2)=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=3)=[CH:30][CH:29]=1

Participants

5

Reactant 4

HCID 949N,N-DimethylanilineHCID 7237O-XyleneHCID 8857Ethyl AcetateHCID 108243-Methoxyaniline

Product 1

HCID 123989986-Methoxy-2-(4-methoxyphenyl)-1H-indole

Conditions

Temperature
170 °C

Procedure

A solution of 33 grams (0.16 mole) of 4-methoxy-bromacetophenone in 230 ml of xylene was dropped into a mixture of 54.5 grams (0.45 mole) of m-anisidine and 76 ml of N,N-dimethyl aniline which was heated to 170° C. bath temperature. After cooling the mixture was treated with ethyl acetate and extracted by shaking with 2N HCl. The aqueous phase was again terated with ethyl acetate and the combined organic phases extracted by shaking several times with 2N HCl. After washing with water and drying the solvent was removed in a vacuum. The crystalline residue was washed colorless with a little ethyl acetate. Yield: 18.8 grams, M.P. 228°-230° C.

Workup

  1. temperatureAfter cooling the mixture
  2. extractionextracted
  3. extractionthe combined organic phases extracted
  4. stirringby shaking several times with 2N HCl
  5. washAfter washing with water
  6. customdrying the solvent
  7. customwas removed in a vacuum
  8. washThe crystalline residue was washed colorless with a little ethyl acetate

Sources & evidence

ORD record
ord-a75ab50cc9e24bbab0509ce060478731
Source dataset
uspto-grants-1985_09
Patent number
US04543360

Reaction notes

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