Chlorosuccinimide → Methyl 2-amino-5-chloro-3-methoxybenzoate

HRID 1186092Notes

Reaction equation

HRID 1186092 reaction equation
[NH2:1][C:2]1[C:11]([O:12][CH3:13])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[Cl:14]N1C(=O)CCC1=O>CN(C)C=O.C(OCC)(=O)C>[NH2:1][C:2]1[C:11]([O:12][CH3:13])=[CH:10][C:9]([Cl:14])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

5

Reactant 2

HCID 31398ChlorosuccinimideHCID 602320Methyl 2-amino-3-methoxybenzoate

Product 1

HCID 58566618Methyl 2-amino-5-chloro-3-methoxybenzoateYield 96.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To methyl 2-amino-3-methoxybenzoate (750 mg, 4.1 mmol) in anhydrous N,N-dimethylformamide (15 mL) was added N-chlorosuccinimide (580 mg, 4.35 mmol) and this mixture was stirred at ambient temperature for 2 hours. The temperature was increased to 60° C. for 4 hours. The deep red solution was cooled, diluted with ethyl acetate, washed with saturated sodium bicarbonate, water, then brine, dried with sodium sulfate, decanted and concentrated to yield crude methyl 2-amino-5-chloro-3-methoxybenzoate (0.85 g, 95%). MS (m/z): 216.1 (M+H)+.

Workup

  1. temperatureThe temperature was increased to 60° C. for 4 hours
  2. temperatureThe deep red solution was cooled
  3. washwashed with saturated sodium bicarbonate, water
  4. dry with materialbrine, dried with sodium sulfate
  5. customdecanted
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-2345dae4507c49469a3fecf8cf0d36d1
Source dataset
uspto-grants-2014_03
Patent number
US08673897B2

Reaction notes

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