4-Nitrophenyl chloroformate → HCID 12805029, compound

HRID 1649095Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]([CH3:15])[CH2:10][C:11](=[O:14])[NH:12][N:13]=2)=[CH:4][CH:3]=1.Cl[C:17]([O:19][C:20]1[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=1)=[O:18]>O1CCCC1>[CH3:15][CH:9]1[C:8]([C:5]2[CH:6]=[CH:7][C:2]([NH:1][C:17]([O:19][C:20]3[CH:21]=[CH:22][C:23]([N+:26]([O-:28])=[O:27])=[CH:24][CH:25]=3)=[O:18])=[CH:3][CH:4]=2)=[N:13][NH:12][C:11](=[O:14])[CH2:10]1

Participants

Conditions

Temperature: 60 °C

Procedure

5.0 g (24.6 millimoles) of 6-(p-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone are dissolved in 150 ml of absolute tetrahydrofuran by heating to 60° C., with stirring. The solution is allowed to cool to room temperature, 5.0 g (24.8 millimoles) of p-nitrophenyl chloroformate are added and the mixture is stirred first for 20 hours at room temperature and then for 5 hours under reflux. It is then concentrated to about 70 ml, 100 ml of water are added and the product is filtered off and recrystallized from dimethylformamide/water at room temperature, giving 6.5 g (72% of theory) of 4,5-dihydro-5-methyl-6-[p-(p-nitrophenoxycarbonylamino)-phenyl]-3(2H)-pyridazinone as yellow crystals, of melting point 177°-178° C.

Workup

temperatureto cool to room temperature
stirringthe mixture is stirred first for 20 hours at room temperature
temperaturefor 5 hours under reflux
concentrationIt is then concentrated to about 70 ml, 100 ml of water
additionare added
filtrationthe product is filtered off
customrecrystallized from dimethylformamide/water at room temperature

Sources & evidence

ORD record: ord-3b55970b2bb04ae9a236b73ec8afc6ab
Source dataset: uspto-grants-1983_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04415571

Reaction notes

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