Hydrochloric Acid → 2-Methyl-4-aminobiphenyl hydrochloride

HRID 413497Notes

Reaction equation

HRID 413497 reaction equation
O.[ClH:2].[CH3:3][C:4]1[CH:9]=[C:8]([NH:10]C(C)=O)[CH:7]=[CH:6][C:5]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(O)(=O)C>[ClH:2].[CH3:3][C:4]1[CH:9]=[C:8]([NH2:10])[CH:7]=[CH:6][C:5]=1[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 111721562-Methyl-4-acetaminobiphenyl

Product 1

HCID 185334912-Methyl-4-aminobiphenyl hydrochloride

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

300 g of water and 296 g of HCl (37%) are added to the 2-methyl-4-acetaminobiphenyl prepared as described in Example 1. Any chlorobenzene still present is distilled off azeotropically, and the mixture is subsequently refluxed until HPLC monitoring indicates complete conversion (about 4 hours). The suspension obtained can be reacted further without further purification and without removal of the acetic acid formed as coproduct in the cleavage. The yield is (calculated from HPLC percentages by area) 99%.

Workup

  1. customprepared
  2. distillationAny chlorobenzene still present is distilled off azeotropically
  3. temperaturethe mixture is subsequently refluxed until HPLC monitoring
  4. customconversion (about 4 hours)
  5. customThe suspension obtained can
  6. customformed as coproduct in the cleavage

Sources & evidence

ORD record
ord-8a894b2f7d324691a6aeecead6b50a5b
Source dataset
uspto-grants-2003_05
Patent number
US06566546B2

Reaction notes

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