Benzyl chloroformate → HCID 54216864, compound

HRID 1456297Notes

Reaction equation

HRID 1456297 reaction equation
Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].[NH2:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[N:19]=[CH:18][CH:17]=[CH:16]2.[OH-].[Na+]>O.C1COCC1>[CH2:5]([O:4][C:2]([NH:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[N:19]=[CH:18][CH:17]=[CH:16]2)=[O:3])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 3

HCID 10387Benzyl chloroformateHCID 113736-AminoquinolineHCID 14798Sodium Hydroxide

Product 1

HCID 54216864HCID 54216864, compoundYield 60.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

13.0 ml (76.28 mmol) of benzyl chloroformate are added dropwise to a stirred solution, cooled to 0° C. of 10.0 g (69.36 mmol) of 6-aminoquinoline in 160 ml of water and 80 ml of THF in the course of 30 minutes, the pH being kept at 10 by simultaneous addition of a 4N NaOH solution. The mixture is subsequently stirred at 0° C. for a further 2 hours, the THF is evaporated off in vacuo and the residue is extracted with 3×50 ml of ethyl acetate. The combined organic extracts are dried over MgSO4, the solvent is evaporated off in vacuo and the residue is purified by chromatography over 450 g of silica gel (toluene:ethyl acetate 1:4). 11.60 g (60%) of the title compound are obtained as crystals.

Workup

  1. customthe THF is evaporated off in vacuo
  2. extractionthe residue is extracted with 3×50 ml of ethyl acetate
  3. dry with materialThe combined organic extracts are dried over MgSO4
  4. customthe solvent is evaporated off in vacuo
  5. customthe residue is purified by chromatography over 450 g of silica gel (toluene:ethyl acetate 1:4)

Sources & evidence

ORD record
ord-bb04d0a6fe564b73bf694d9f2bbfc3ae
Source dataset
uspto-grants-1998_12
Patent number
US05843967

Reaction notes

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