Water → HCID 57898840, compound

HRID 217294Notes

Reaction equation

HRID 217294 reaction equation
[Cl:1]N1C(=O)CCC1=O.[CH3:9][O:10][C:11]([CH2:13][C:14]1[CH:23]=[C:22]([NH2:24])[CH:21]=[CH:20][C:15]=1[C:16]([O:18][CH3:19])=[O:17])=[O:12].O.COC(CC1C(Cl)=C(N)C=CC=1C(OC)=O)=O>C(#N)C>[CH3:9][O:10][C:11]([CH2:13][C:14]1[CH:23]=[C:22]([NH2:24])[C:21]([Cl:1])=[CH:20][C:15]=1[C:16]([O:18][CH3:19])=[O:17])=[O:12]

Participants

6

Reactant 4

HCID 962WaterHCID 31398ChlorosuccinimideHCID 12616213HCID 12616213, compoundHCID 68906482HCID 68906482, compound

Product 1

HCID 57898840HCID 57898840, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N-Chlorosuccinimide (1.0 g, 7.3 mmol) was added to a solution of methyl 2-methoxycarbonylmethyl-4-aminobenzoate (1.5 g, 6.6 mmol) in acetonitrile (10 mL). The mixture was stirred while heating under reflux for 1 hour. After the reaction solution was cooled to room temperature, water was added thereto and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. Then, the resulting solid was washed with ethyl acetate to give a 0.9:1 mixture of the title compound and methyl 2-methoxycarbonylmethyl-4-amino-3-chlorobenzoate (1.5 g, 88%).

Workup

  1. temperaturewhile heating
  2. temperatureunder reflux for 1 hour
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. washThen, the resulting solid was washed with ethyl acetate
  7. customto give

Sources & evidence

ORD record
ord-2b3298f3ac3e4a768008c13db9c98eed
Source dataset
uspto-grants-2012_06
Patent number
US08193351B2

Reaction notes

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