Hydrochloric Acid → 5-Methoxy-2-(pyridin-2-yl)aniline

HRID 477044Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)=[C:5]([N+:15]([O-])=O)[CH:4]=1.Cl.[OH-].[Na+]>C(O)C>[NH2:15][C:5]1[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=[CH:7][C:6]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1

Participants

Conditions

Temperature: 100 °C

Procedure

1.63 g of 2-(4-methoxy-2-nitrophenyl)pyridine was dissolved in 14 ml of ethanol, and 8 g of stannous chloride dihydrate and 5.7 ml of concentrated hydrochloric acid were added. The mixture was stirred at a bath temperature of 100° C. for 3 hours. After cooling, the reaction mixture was made alkaline with a 50% aqueous solution of sodium hydroxide and extracted with benzene. The solvent was evaporated. The resulting dark brown oil was subjected to silica gel column chromatography and the column was eluted with chloroform. As a yellow oil, 967 mg (yield 68.2%) of 2-(2-amino-4-methoxyphenyl)pyridine was obtained.

Workup

temperatureAfter cooling
extractionextracted with benzene
customThe solvent was evaporated
washthe column was eluted with chloroform

Sources & evidence

ORD record: ord-462921381ab24d8c83b51decc967a231
Source dataset: uspto-grants-1989_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04886822

Reaction notes

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