Acetic Acid → Methyl 2-amino-5-chlorobenzoate

HRID 550771Notes

Reaction equation

HRID 550771 reaction equation
C(O)(=O)C.[NH2:5][C:6]1[CH:15]=[CH:14][CH:13]=[CH:12][C:7]=1[C:8]([O:10][CH3:11])=[O:9].[Cl:16][O-].[Ca+2].Cl[O-]>ClCCl>[NH2:5][C:6]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:7]=1[C:8]([O:10][CH3:11])=[O:9]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 8635Methyl AnthranilateHCID 24504Calcium hypochlorite

Product 1

HCID 78878Methyl 2-amino-5-chlorobenzoateYield 65.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1 liter of glacial acetic acid and 10 liters of ice-water are added to a solution of 2.0 kg of methyl 2-aminobenzoate in 15 liters of dichloromethane. 1.9 kg of calcium hypochlorite are added at 10° with vigorous stirring, during which the temperature should not rise above 15°. The mixture is stirred for a further 6 hours and left to stand for 16 hours. The dichloromethane is separated off, the aqueous phase is washed with dichloromethane, and the combined organic phases are washed with a 10% Na2SO3 solution (warming!). The combined dichloromethane phases are stirred with 2 kg of silica gel, 200 g of activated carbon and 2 kg of sodium sulfate. The phases are separated, the dichloromethane is removed, 10 liters of nhexane are added, the mixture is left to stand at 0-5° for 16 hours, and the product is separated off, giving 1.6 kg of methyl 2-amino-5-chlorobenzoate (“1”).

Workup

  1. customrise above 15°
  2. waitleft
  3. waitto stand for 16 hours
  4. customThe dichloromethane is separated off
  5. washthe aqueous phase is washed with dichloromethane
  6. washthe combined organic phases are washed with a 10% Na2SO3 solution (warming!)
  7. stirringThe combined dichloromethane phases are stirred with 2 kg of silica gel, 200 g of activated carbon and 2 kg of sodium sulfate
  8. customThe phases are separated
  9. customthe dichloromethane is removed
  10. addition10 liters of nhexane are added
  11. waitthe mixture is left
  12. waitto stand at 0-5° for 16 hours
  13. customthe product is separated off

Sources & evidence

ORD record
ord-2343dd6156614c16bc9daae9fc553263
Source dataset
uspto-grants-2011_05
Patent number
US07947696B2

Reaction notes

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