Aniline → 2-Aminobiphenyl

40 mmol of an aniline derivative (III) were suspended or dissolved in a mixture of 20 ml of water, 8 ml of 10% by weight aqueous hydrochloric acid and 8 ml of a 1M solution of titanium(III) chloride in 16 ml of 10% by weight aqueous hydrochloric acid (48 mmol of HCl). To this suspension or solution were added, at room temperature, 2 mmol of the tetrafluoroborate salt of a diazonium compound (II) in small portions as a solid over a period of 10 minutes. Once the mixture thus formed had been stirred for a further 15 minutes, a solution of 4.0 g of sodium hydroxide and 4.0 g of sodium sulfite in 40 ml of water was added. The reaction mixture was extracted three times with diethyl ether and the combined organic phases were then washed with saturated sodium chloride solution and dried over sodium sulfate. After the crude product had been concentrated under reduced pressure and purified by column chromatography, the 2-aminobiphenyl was obtained as a light brown oil.

1. additionTo this suspension or solution were added, at room temperature
2. customOnce the mixture thus formed
3. extractionThe reaction mixture was extracted three times with diethyl ether
4. washthe combined organic phases were then washed with saturated sodium chloride solution
5. dry with materialdried over sodium sulfate
6. concentrationAfter the crude product had been concentrated under reduced pressure
7. custompurified by column chromatography

ORD record

ord-ed936086d8124f0a829fbde1fc379b53

Source dataset

uspto-grants-2014_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08637707B2