5-(Benzyloxy)-2-methoxyaniline → 4-Benzyloxy-2,3-dimethyl-7-methoxyindole

HRID 1707754Notes

Reaction equation

HRID 1707754 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:13]([O:16][CH3:17])=[CH:14][CH:15]=1)[NH2:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CN(C)C=O>[CH2:1]([O:8][C:9]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:11]2[C:10]=1[C:2]([CH3:1])=[C:3]([CH3:4])[NH:12]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 156769785-(Benzyloxy)-2-methoxyaniline

Product 1

HCID 189625274-Benzyloxy-2,3-dimethyl-7-methoxyindole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

1 mole (229 g) of 3-benzyloxy-6-methoxyaniline is added to 700 ml of dimethylformamide and 0.5 mole (76 g) of 2-bromobutanone. The reaction medium is heated to 40° C. for 2 hours 30 minutes and then to 120° C. for three quarters of an hour. By adding ice and then cooling, an oil is obtained which is decanted and then dissolved in ethyl acetate. After washing with a 2N solution of hydrochloric acid, then with water and evaporation of the ethyl acetate, the desired product is obtained in the form of a dry extract which is recrystallized from cyclohexane under reflux. The desired product melts at 100° C.

Workup

  1. customto 120° C.
  2. customfor three quarters of an hour
  3. additionBy adding ice
  4. temperaturecooling
  5. customan oil is obtained which
  6. customis decanted
  7. dissolutiondissolved in ethyl acetate
  8. washAfter washing with a 2N solution of hydrochloric acid
  9. customwith water and evaporation of the ethyl acetate

Sources & evidence

ORD record
ord-705f6258ca6341aea1f2a2abf20d4dd9
Source dataset
uspto-grants-1994_10
Patent number
US05354870

Reaction notes

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