Isopropenyl chloroformate → (2RS)-1-(Isopropenyloxycarbonyl)-2-methyl-1,2-dihydro-1,4,6-triazanaphthalen-3(4H)-one

HRID 21530

Reaction equation

HRID 21530 reaction equation
[CH3:1][CH:2]1[C:11](=[O:12])[NH:10][C:9]2[C:4](=[CH:5][CH:6]=[N:7][CH:8]=2)[NH:3]1.Cl[C:14]([O:16][C:17]([CH3:19])=[CH2:18])=[O:15]>N1C=CC=CC=1>[C:17]([O:16][C:14]([N:3]1[C:4]2[C:9](=[CH:8][N:7]=[CH:6][CH:5]=2)[NH:10][C:11](=[O:12])[CH:2]1[CH3:1])=[O:15])([CH3:19])=[CH2:18]

Participants

4

Reactant 2

HCID 93846Isopropenyl chloroformateHCID 199328812-methyl-1H,2H,3H,4H-pyrido[3,4-b]pyrazin-3-one

Product 1

HCID 19932849(2RS)-1-(Isopropenyloxycarbonyl)-2-methyl-1,2-dihydro-1,4,6-triazanaphthalen-3(4H)-oneYield 12%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

(2RS)-2-Methyl-1,2-dihydro-1,4,6-triazanaphthalen-3(4H)-one (A. Albert, G. B. Barlin J. Chem. Soc. 1963, 5156) (570 mg, 3.5 mmol) was dissolved in 30 ml of anhydrous pyridine and cooled in an ice bath. 0.42 ml (3.8 mmol) of isopropenyl chloroformate was added dropwise, and the mixture was subsequently stirred at room temperature overnight. Concentration, chromatography on silica gel (ethyl acetate/methanol=20:1) and crystallization (pentane/diethyl ether) resulted in 100 mg (12%) of the desired product of melting point 170°-171° C.

Workup

  1. temperaturecooled in an ice bath
  2. concentrationConcentration, chromatography
  3. customon silica gel (ethyl acetate/methanol=20:1) and crystallization (pentane/diethyl ether)

Sources & evidence

ORD record
ord-51bf8dc81a7448649807c64ccbba7baf
Source dataset
uspto-grants-1995_06
Patent number
US05424311

Linked notes

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