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Water → 2,2,2-Trichloroethyl isoquinolin-4-ylcarbamate

HRID 2262957
Notes
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Reaction equation

HRID 2262957 reaction equation
N[C:2]1[N:3]=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[N:12]1C=CC=CC=1.Cl[C:19]([O:21][CH2:22][C:23]([Cl:26])([Cl:25])[Cl:24])=[O:20].O>O1CCCC1>[CH:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:11]([NH:12][C:19](=[O:20])[O:21][CH2:22][C:23]([Cl:26])([Cl:25])[Cl:24])=[CH:2][N:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 870632,2,2-Trichloroethyl chloroformateHCID 311869Isoquinolin-3-Amine

Product 1

HCID 687756952,2,2-Trichloroethyl isoquinolin-4-ylcarbamate

Reagents, catalysts & solvents 1

HCID 8028Tetrahydrofuran
Solvent

Procedure

To a solution of 3-aminoisoquinoline (1.00 g, 6.94 mmol) and pyridine (0.660 ml, 8.32 mmol) in tetrahydrofuran (23 ml) was added, under ice-cooling, 2,2,2-trichloroethyl chloroformate (1.15 ml, 8.32 mmol), and the mixture was stirred at room temperature for 1 hour and half. Water was poured to the reaction mixture, and the resulting solution was extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. Hexane was poured to the residue, and 2.03 g (91.7%) of the desired product as a solid was separated by filtration.

Workup

  1. temperaturecooling
  2. extractionthe resulting solution was extracted with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. additionHexane was poured to the residue, and 2.03 g (91.7%) of the desired product as a solid
  7. customwas separated by filtration

Sources & evidence

ORD record
ord-53dd4dfc4d704079bc175bb15435aa83
Source dataset
uspto-grants-2010_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07851473B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes