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

HRID 377867Notes

Reaction equation

HRID 377867 reaction equation
[NH2:1][C:2]1[C:3]([O:12][CH3:13])=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.Cl[C:15]([O:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:16]>ClCCl>[CH3:13][O:12][C:3]1[C:2]([NH:1][C:15](=[O:16])[O:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=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 218028652-Methoxyquinolin-3-amine

Product 1

HCID 19356985Phenyl N-(2-methoxyquinolin-3-yl)carbamateYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Amino-2-methoxyquinoline(4 g, 23 mmol) and phenyl chloroformate(4.04 g, 25 mmol) were dissolved in dichloromethane and stirred at room temperature for 2 hours. The above mixture was concentrated under the reduced pressure to remove dichloromethane and purified by column chromatography(hexane:ether=8:1) to obtain the titled compound.

Workup

  1. concentrationThe above mixture was concentrated under the reduced pressure
  2. customto remove dichloromethane
  3. custompurified by column chromatography(hexane:ether=8:1)

Sources & evidence

ORD record
ord-7b7776045b854099897ef6db1e5236f6
Source dataset
uspto-grants-2000_02
Patent number
US06028195

Reaction notes

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