Iodine → 4-methoxy-2-methyl-N-phenylaniline

HRID 1065607Notes

Reaction equation

HRID 1065607 reaction equation
COC1C=C(C)C(NC(=O)C)=CC=1.BrC1C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+].II.[CH3:29][O:30][C:31]1[CH:32]=[C:33]([CH3:47])[C:34]([N:37](C(=O)C)[C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)=[CH:35][CH:36]=1.[OH-].[Na+]>[Cu].O>[CH3:29][O:30][C:31]1[CH:32]=[C:33]([CH3:47])[C:34]([NH:37][C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=2)=[CH:35][CH:36]=1

Participants

9

Reactant 6

HCID 807IodineHCID 7961BromobenzeneHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 95082N-(4-Methoxy-2-methylphenyl)-acetamideHCID 136688303-methoxy-6-(N-acetylanilino) toluene

Product 1

HCID 1624614-methoxy-2-methyl-N-phenylanilineYield 90.5%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 962WaterSolvent

Conditions

Temperature
180 °C

Procedure

24 g. of 3-methoxy-6-acetylaminotoluene, 31.6 g. of bromobenzene, 10.38 g. of potassium carbonate, 0.6 g. of copper powder and 0.01 g. of iodine were refluxed under ordinary pressure on the oil bath for 48 hours. Then excess bromobenzene was recovered by means of steam distillation, and the reamining reaction mixture was distilled in a vacuum to obtain 29.2 g. (85.0 percent of theoretical yields) of 3-methoxy-6-(N-acetylanilino) toluene as a light yellowish brown solid having a melting point at 86° to 87° C., having the formula: ##STR12## 25 g. of this intermediate was hydrolyzed by heating at 180° C. for 8 hours in the autoclave, together with 130 ml. of water and 9 g. of caustic soda. After cooling, the reaction product was filtered to collect a solid and thereafter recrystallized by using a double amount of ethyl alcohol. 18.8 g. (90.5 percent of theoretical yields) of 3-methoxy-6-anilinotoluene was obtained as light brown crystals having a melting point of 79° to 80.5° C.

Workup

  1. distillationThen excess bromobenzene was recovered by means of steam distillation
  2. customthe reamining reaction mixture
  3. distillationwas distilled in a vacuum
  4. customto obtain 29.2 g
  5. customat 86° to 87° C.
  6. temperatureAfter cooling
  7. filtrationthe reaction product was filtered
  8. customto collect a solid
  9. customrecrystallized

Sources & evidence

ORD record
ord-2a1178b52cf845b98f409d00427ef66a
Source dataset
uspto-grants-1982_05
Patent number
US04330473

Reaction notes

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