Potassium Hydroxide → HCID 22903586, compound

HRID 1488961Notes

Reaction equation

Cl[C:2]1[CH:3]=[C:4]([C:6]([N+:10]([O-:12])=[O:11])=[CH:7][C:8]=1[Cl:9])[NH2:5].[OH:13][C:14]1[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=1.[OH-].[K+]>CS(C)=O>[Cl:9][C:8]1[CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[C:4]([NH2:5])=[CH:3][C:2]=1[N:17]1[CH:18]=[CH:19][C:14](=[O:13])[CH:15]=[CH:16]1

Participants

Conditions

Temperature: 130 °C

Procedure

First, a mixture containing 14.3 g of 3,4-dichloro-6-nitroaniline, 9.01 g of 4-hydroxypyridine, 5.87 g of 86% potassium hydroxide, and 70 ml of dimethylsulfoxide was heated in an oil bath at 130° C. for 3.5 hours, and cooled. Ice water was added to the mixture and precipitated crystals were filtered. Then, 16.9 g of the resultant crude crystals were applied to a column containing 100 g of silica gel and eluted with 10% methanol in chloroform. The eluate was combined and evaporated. The residue was filtered to give 9.78 g of crude crystals of 4-chloro-3-(4-oxo-4H-pyridin-1-yl)-6-nitroaniline (melting point: 288° to 291° C. (decomposition)). Then, 300 mg of the crude crystals were recrystallized with methanol to give 268 mg of crystals of 4-chloro-3-(4-oxo-4H-pyridin-1-yl)-6-nitroaniline.

Workup

temperaturecooled
customprecipitated crystals
filtrationwere filtered
additioncontaining 100 g of silica gel
washeluted with 10% methanol in chloroform
customevaporated
filtrationThe residue was filtered
customto give 9.78 g of crude crystals of 4-chloro-3-(4-oxo-4H-pyridin-1-yl)-6-nitroaniline (melting point: 288° to 291° C. (decomposition))
customThen, 300 mg of the crude crystals were recrystallized with methanol

Sources & evidence

ORD record: ord-ad2d34065f20412ca3120829e0966caa
Source dataset: uspto-grants-1997_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05677305

Reaction notes

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