Phenyl chloroformate → Phenyl N-(2-methylquinolin-3-yl)carbamate

HRID 377892Notes

Reaction equation

HRID 377892 reaction equation
[NH2:1][C:2]1[C:3]([CH3:12])=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.Cl[C:14]([O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:15]>C(Cl)Cl>[CH3:12][C:3]1[C:2]([NH:1][C:14](=[O:15])[O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1

Participants

4

Reactant 2

HCID 15891Phenyl chloroformateHCID 123006962-Methylquinolin-3-amine

Product 1

HCID 19356949Phenyl N-(2-methylquinolin-3-yl)carbamateYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-amino-2-methylquinoline(4 g, 25 mmol) and phenyl chloroformate(4.04 g, 25 mmol) were dissolved in methylene chloride and then was stirred at room temperature for 2 hrs. The mixture solution was concentrated under the reduced pressure to remove methylene chloride and purified by column chromatography(ethylacetate:hexane=1:10) to obtain the titled compound.

Workup

  1. concentrationThe mixture solution was concentrated under the reduced pressure
  2. customto remove methylene chloride
  3. custompurified by column chromatography(ethylacetate:hexane=1:10)

Sources & evidence

ORD record
ord-4d32dbc01ca24c418803381dafd2e4c0
Source dataset
uspto-grants-2000_02
Patent number
US06028195

Reaction notes

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