M-Phenylenediamine → 2(1H)-Pyrazinone, 3-[(3-aminophenyl)amino]-5-bromo-1-methyl-

HRID 592902Notes

Reaction equation

HRID 592902 reaction equation
Br[C:2]1[C:3](=[O:10])[N:4]([CH3:9])[CH:5]=[C:6]([Br:8])[N:7]=1.[C:11]1([NH2:18])[CH:16]=[CH:15][CH:14]=[C:13]([NH2:17])[CH:12]=1.C(N(CC)CC)C>C(O)(C)C>[NH2:17][C:13]1[CH:12]=[C:11]([NH:18][C:2]2[C:3](=[O:10])[N:4]([CH3:9])[CH:5]=[C:6]([Br:8])[N:7]=2)[CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 7935M-PhenylenediamineHCID 8471TriethylamineHCID 130629693,5-Dibromo-1-methyl-1H-pyrazin-2-one

Product 1

HCID 866844042(1H)-Pyrazinone, 3-[(3-aminophenyl)amino]-5-bromo-1-methyl-Yield 81.3%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 3,5-dibromo-1-methylpyrazin-2(1H)-one (536 mg, 2.0 mmol) and benzene-1,3-diamine (324 mg, 3.0 mmol) in isopropanol (18 mL) was added triethylamine (2.8 mL). The reaction mixture was stirred at 80° C. overnight. Then the mixture was evaporated under reduced pressure to afford 219a (480 mg, 81%) as a white solid. MS-ESI: [M+H]+ 295.0

Workup

  1. customThen the mixture was evaporated under reduced pressure

Sources & evidence

ORD record
ord-8c5da55b3f654c0d859c2d76b2d8a6ea
Source dataset
uspto-grants-2016_01
Patent number
US09238655B2

Reaction notes

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