O-aminobiphenyls

Amino 2 deoxy d glucose, conversion of hydrochloride to 2 acetamido-2 deoxy d glucose, 46, 2 l-(Ammomcthyl) cycloheptanol, 46, 31 2 Amino 2 methyl 1 propanol in isolation of levopimanc acid 45, 64 c-Amino p nitrobiphenyl, by nitration of o aminobiphenyl, 46, 86 from o,p dimtrobiphenyl, 46, 88 Amino 2 propanone, semicarbazone... 

Nicotinic anhydridf, 47, 89 Nitration of o aminobiphenyl to o-amino p -nitrobipheny 1, 46, 86 of o Lolumlrilc with minimum lelra-fluoroboiate, 47, 56... 

Phenanthridine cyclization by dehydrative ring closure of acyl-o-aminobiphenyls with phosphorus oxychloride in boiling nitrobenzene. 

A. o-Aminobiphenyl. A Parr bottle is charged with 60 g. (0.30 mole) of o-nitrobiphenyl (Note 1), 3 g. of 5% palladium-on-carbon catalyst (Note 2), and 200 ml. of 95% ethanol. The mixture is shaken with hydrogen under 25-50 p.s.i. until the gas is no longer absorbed (about 70 minutes), the catalyst is filtered from the hot solution and washed with 20 ml. of ethanol, and the filtrates are poured in a thin stream into 11. of ice water contained... 

B. o-Amino-p -nitrobiphenyl. Concentrated sulfuric acid (400 ml.) is placed in a 11. round-bottomed flask fitted with a mechanical stirrer and a thermometer. Stirring is begun, and 45.0 g. (0.27 mole) of powdered o-aminobiphenyl is added all at once through a powder funnel. When the amine has dissolved, the flask is placed in an ice-salt bath and its contents cooled to a temperature between 0° and —5°. A mixture of 30 ml. of concentrated sulfuric acid and 11.0 ml. of fuming nitric acid (density... 

The decomposition of o-azidobiphenyls is a convenient and general synthesis for a variety of carbazoles in good yield,16 especially those not available through direct substitution of car-bazole itself. Many of the required intermediates can be prepared from o-aminobiphenyl by substitution reactions. The method is also applicable to the preparation of analogs of the carbazole system in which a heterocyclic ring replaces a benzene... 

Many aldehydes separated by TLC produce fluorescent spots after treatment with o-aminobiphenyl dissolved in dilute sulfuric acid [142]. 

Lewis—Smith o-Aminobiphenyl (0.3 g dissolved in 100 ml of a 19 1 ethanol/phosphoric acid mixture) is sprayed on the plate, which is then heated at 110°C (15 min). 

A solution of 20 g. (0.12 mole) of o-aminobiphenyl in hydrochloric acid is diazotized in the usual manner [Org. Syntheses Coll. Vol. 1, 170 (1941)], and the solution of the diazonium salt is added to a solution of cuprous cyanide prepared from 35 g. of copper sulfate [Org. Syntheses Coll. Vol. 1, 514 (1941)]. When evolution of nitrogen ceases, the mixture is warmed for 30 minutes on a water bath and then made alkaline with sodium hydroxide. The mixture is steam-distilled, and the distillate is agitated with stannous chloride solution. SuflBcient sodium hydroxide is added to precipitate the tin, and the mixture is extracted with ether. The ethereal solution is dried and distilled to give 11.0 g. (50%) of o-cyanobiphenyl boiling at 174°/13 mm., m.p. 37°. 

Amino-2-methyl-l-propanol in isolation of levopimaric acid, 46, 64 e-Amino- -nitrobiphenyl, by nitration of o-aminobiphenyl, 46,86 from o,/> -dinitrobiphenyl, 46, 88 AmiNO-2-PIIOPANONE, SEiaCABSAZONE HYDROCSIAtiaOE, 46,1 Ammonia, reaction with 3,4-dichloto-... 

A solution of 1 molar equivalent of o-aminobiphenyl in toluene is added to a 20-30% solution of phosgene in toluene containing 6 molar equivalents of phosgene. Caution—toxic gas—use hood with good... 

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