Chlorosuccinimide → Methyl 3-amino-6-chloro-2-methylbenzoate

HRID 1639787Notes

Reaction equation

HRID 1639787 reaction equation
[NH2:1][C:2]1[C:3]([CH3:12])=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[Cl:13]N1C(=O)CCC1=O>CN(C)C=O>[NH2:1][C:2]1[C:3]([CH3:12])=[C:4]([C:9]([Cl:13])=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 38010253-Amino-2-methylbenzoic acid methyl ester

Product 1

HCID 21710154Methyl 3-amino-6-chloro-2-methylbenzoateYield 45%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl 3-amino-2-methylbenzoate (25.0 g, 151 mmol) in N,N-dimethylformamide (757 mL) was added N-chlorosuccinimide (20.2 g, 151 mmol) at room temperature, and the mixture was stirred for 3 days. The reaction mixture was concentrated under reduced pressure to a half volume, and the mixture was extracted with dichloromethane. The extract was dried over anhydrous sodium sulfate and the solvent was evaporated under reduced pressure. The residue was purified by flash silica gel column chromatography (ethyl acetate/hexane=1/5) to give the title compound (13.5 g, yield 45%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure to a half volume
  2. extractionthe mixture was extracted with dichloromethane
  3. dry with materialThe extract was dried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by flash silica gel column chromatography (ethyl acetate/hexane=1/5)

Sources & evidence

ORD record
ord-f53ad9e9c67c4403beb4bf59a0c752cb
Source dataset
uspto-grants-2012_02
Patent number
US08110585B2

Reaction notes

Loading…