Ethyl chloroformate → HCID 13630999, compound

HRID 1981528Notes

Reaction equation

HRID 1981528 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH2:6][CH2:5]2.C(=O)([O-])[O-].[K+].[K+].[C:19](Cl)(=[O:23])[O:20][CH2:21][CH3:22]>O.CC(C)=O>[CH2:21]([O:20][C:19]([NH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH2:6][CH2:5]2)=[O:23])[CH3:22]

Participants

6

Reactant 3

HCID 10928Ethyl chloroformateHCID 11430Potassium CarbonateHCID 49127596-amino-3,4-dihydroquinolin-2(1H)-one

Product 1

HCID 13630999HCID 13630999, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent2×

Procedure

6-Amino-3,4-dihydrocarbostyril (60 g) is added to a solution of potassium carbonate (128 g) in water (300 ml) and acetone (300 ml), and thereto is added dropwise ethyl chlorocarbonate (46 ml) with stirring under ice-cooling. After the addition, the mixture is further reacted at the same temperature for 30 minutes. After the reaction, the reaction mixture is poured into water, and the resulting precipitate is separated by filtration, washed with water and further with diethyl ether. After drying, the crystal thus obtained is purified by silica gel column chromatography (solvent; chloroform:methanol=100:1) and then recrystallized from ethanol to give 6-ethoxycarbonylamino-3,4-dihydrocarbostyril (68.5 g), as colorless prisms, m.p. 193°-194° C.

Workup

  1. temperaturecooling
  2. additionAfter the addition
  3. customthe mixture is further reacted at the same temperature for 30 minutes
  4. customAfter the reaction
  5. customthe resulting precipitate is separated by filtration
  6. washwashed with water and further with diethyl ether
  7. customAfter drying
  8. customthe crystal thus obtained
  9. customis purified by silica gel column chromatography (solvent; chloroform:methanol=100:1)
  10. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-0b7b9e8ecea34a6f91a0d31f882eb2be
Source dataset
uspto-grants-1986_06
Patent number
US04593035

Reaction notes

Loading…