Hydrochloric Acid → Benzenamine, 4,5-dichloro-2-methoxy-

HRID 893204Notes

Reaction equation

HRID 893204 reaction equation
CC(C)(C)C([NH:5][C:6]1[CH:11]=[C:10]([Cl:12])[C:9]([Cl:13])=[CH:8][C:7]=1[O:14][CH3:15])=O.Cl>C(O)C>[Cl:13][C:9]1[C:10]([Cl:12])=[CH:11][C:6]([NH2:5])=[C:7]([O:14][CH3:15])[CH:8]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 190968852,2-dimethyl-N-(4,5-dichloro-2-methoxyphenyl)propanamide

Product 1

HCID 6453986Benzenamine, 4,5-dichloro-2-methoxy-

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The 2,2-dimethyl-N-(4,5-dichloro-2-methoxyphenyl)propanamide (3.70 grams, 0.01 mole) prepared in Part B was dissolved in ethanol: 12N HCl (1:1), the mixture heated under reflux overnight and then freed of volatiles under rotary evaporation. Partition between 2N HCl and dichloromethane gave and acid-soluble fraction which was worked up to give 1.1 grams (0.01 mole) or pure 4,5-dichloro-2-methoxyaniline as determined by thin layer chromatographic analysis. The dichloromethane fraction from above was freed of solvent giving starting material which was again refluxed overnight with ethanol: 12N HCl and worked up to given an additional 1.2 grams (0.01 mole) of pure 4,5-dichloro-2-methoxyaniline as determined by thin layer chromatographic analysis. NMR analysis of the product indicated the following:

Workup

  1. temperatureunder reflux overnight
  2. customfreed of volatiles under rotary evaporation
  3. customPartition between 2N HCl and dichloromethane
  4. customgave

Sources & evidence

ORD record
ord-139f7feed17348b1a83e5d68e778d098
Source dataset
uspto-grants-1992_06
Patent number
US05123951

Reaction notes

Loading…