3,5-Dimethoxyaniline → N-(3,5-dimethoxyphenyl)quinoxaline-2,3-diamine

HRID 331180Notes

Reaction equation

Cl[C:2]1[C:3]([NH2:12])=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[CH3:13][O:14][C:15]1[CH:16]=[C:17]([CH:19]=[C:20]([O:22][CH3:23])[CH:21]=1)[NH2:18]>CN1C(=O)CCC1>[CH3:23][O:22][C:20]1[CH:19]=[C:17]([NH:18][C:2]2[C:3]([NH2:12])=[N:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[N:11]=2)[CH:16]=[C:15]([O:14][CH3:13])[CH:21]=1

Participants

Conditions

Temperature: 145 °C

Procedure

3-chloroquinoxalin-2-amine (1.8 g, 10 mmol) and 3,5-dimethoxyaniline (4.6 g, 30 mmol, commercially available from Aldrich) are taken up in NMP (4.5 ml) and heated to 145° C. in the sealed tube for 3 h under N2. When TLC confirms the total consumption of the starting material, the reaction is cooled to rt and treated with EtOAc (4 ml). The first crop of solid is filtered followed by the 2nd crop. The first is recrystallised from CHCl3: EtOAc and the 2nd crop is washed with EtOAc, to afford 1.8 g (60%) of pure title compound. LC/MS: (ES+): 297.1, (ES−): 295.1.

Workup

customthe total consumption of the starting material
temperaturethe reaction is cooled to rt
additiontreated with EtOAc (4 ml)
filtrationThe first crop of solid is filtered
customThe first is recrystallised from CHCl3
washEtOAc and the 2nd crop is washed with EtOAc

Sources & evidence

ORD record: ord-f15a55ae59784c57888da48d756b0e23
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08877757B2

Reaction notes

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