Pyridine → HCID 86672176, compound

HRID 1843041Notes

Reaction equation

HRID 1843041 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([Cl:12])[CH:3]=1.N1C=CC=CC=1.Cl[C:20]([O:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:21]>C(#N)C>[Cl:12][C:4]1[CH:3]=[C:2]([NH:1][C:20]([O:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:21])[CH:11]=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7]

Participants

5

Reactant 3

HCID 1049PyridineHCID 15891Phenyl chloroformateHCID 11839197Methyl 4-Amino-2-chlorobenzoate

Product 1

HCID 86672176HCID 86672176, compoundYield 106%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Methyl 4-amino-2-chlorobenzoate (407 mg, 2.2 mmol) was dissolved in acetonitrile. To the reaction mixture was added pyridine (0.3 ml, 2.4 mmol) and phenyl chloroformate (0.21 ml, 2.6 mmol) and the mixture was stirred at room temperature for 1 h under N2. TLC showed complete consumption of starting material. The reaction mixture was diluted with water and extracted with EtOAc. The organic layer was washed with water and brine. The organic layer was dried over MgSO4 and concentrated under reduced pressure. The crude product was purified by column chromatography to give pure compound methyl 2-chloro-4-(phenoxycarbonylamino)benzoate (713 mg).

Workup

  1. customconsumption of starting material
  2. additionThe reaction mixture was diluted with water
  3. extractionextracted with EtOAc
  4. washThe organic layer was washed with water and brine
  5. dry with materialThe organic layer was dried over MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-984acc8fbb9e4dd5b8b04b7a445a2cf8
Source dataset
uspto-grants-2015_02
Patent number
US08946204B2

Reaction notes

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