Chlorosuccinimide → HCID 58288449, compound

HRID 1476090Notes

Reaction equation

HRID 1476090 reaction equation
[Cl:1]N1C(=O)CCC1=O.[NH2:9][C:10]1[C:11]([CH3:22])=[C:12]([CH2:16][CH2:17][C:18]([O:20][CH3:21])=[O:19])[CH:13]=[CH:14][CH:15]=1>C(#N)C.C(OCC)(=O)C>[NH2:9][C:10]1[C:11]([CH3:22])=[C:12]([CH2:16][CH2:17][C:18]([O:20][CH3:21])=[O:19])[CH:13]=[CH:14][C:15]=1[Cl:1]

Participants

5

Reactant 2

HCID 31398ChlorosuccinimideHCID 58288216HCID 58288216, compound

Product 1

HCID 58288449HCID 58288449, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

At RT, 1.38 g (10.3 mmol) of N-chlorosuccinimide were added to a solution of 2.0 g (10.3 mmol) of methyl 3-(3-amino-2-methylphenyl)propanoate in 10 ml of acetonitrile. The reaction mixture was stirred for 30 min and then diluted with ethyl acetate. The mixture was washed successively with sat. sodium bicarbonate solution and sat. sodium chloride solution, dried over magnesium sulphate and concentrated under reduced pressure. The crude product gave, after chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 10:1), 279 mg of the target product (11.8% of theory).

Workup

  1. washThe mixture was washed successively with sat. sodium bicarbonate solution and sat. sodium chloride solution
  2. dry with materialdried over magnesium sulphate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8835141c0cc845fbb67169f52a0b5ced
Source dataset
uspto-grants-2015_04
Patent number
US09018414B2

Reaction notes

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