2-Bromopyridine → 2-[(3-Nitro-2,4-dimethylphenyl)-amino]-pyridine

HRID 981860Notes

Reaction equation

[N+:1]([C:4]1[C:5]([CH3:12])=[C:6]([CH:8]=[CH:9][C:10]=1[CH3:11])[NH2:7])([O-:3])=[O:2].Br[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1.C(=O)([O-])[O-].[Na+].[Na+]>O>[N+:1]([C:4]1[C:5]([CH3:12])=[C:6]([NH:7][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)[CH:8]=[CH:9][C:10]=1[CH3:11])([O-:3])=[O:2]

Participants

Conditions

Temperature: 20 °C

Procedure

3.3 g of 3-Nitro-2,4-dimethylaniline and 3.2 g of 2-bromo-pyridine are mixed and the resulting mixture heated for 8 hours to 170° C. After cooling to 20° C., the greasy mass formed was dissolved in water and the solution pH then raised by addition of sodium carbonate. The resulting precipitate was recrystallized from ethanol. 2 g of the product melting at 178° to 179° C. were obtained. Another 2.1 g of the substance were obtained from the aqueous phase by concentration.

Workup

temperaturethe resulting mixture heated for 8 hours to 170° C
customthe greasy mass formed
customThe resulting precipitate was recrystallized from ethanol

Sources & evidence

ORD record: ord-5333816ef9e6458dacbd323df6c64b6c
Source dataset: uspto-grants-1991_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04994087

Reaction notes

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