Hydrochloric Acid → 4'-Chloro-3,5-diethylbiphen-4-ylamine

HRID 72283Notes

Reaction equation

Cl.C(OC(=O)[NH:8][C:9]1[C:14]([CH2:15][CH3:16])=[CH:13][C:12]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)=[CH:11][C:10]=1[CH2:24][CH3:25])(C)(C)C>CO>[Cl:23][C:20]1[CH:21]=[CH:22][C:17]([C:12]2[CH:11]=[C:10]([CH2:24][CH3:25])[C:9]([NH2:8])=[C:14]([CH2:15][CH3:16])[CH:13]=2)=[CH:18][CH:19]=1

Participants

Conditions

Temperature: 60 °C

Procedure

Concentrated hydrochloric acid (22 ml) is added to a solution of (4′-chloro-3,5-diethylbiphen-4-yl)carbamic acid tert-butyl ester (22 g, 0.06 mol) in methanol (110 ml), and the reaction mixture is heated to 60° C. for 2 hours. The mixture is cooled to room temperature and most of the methanol is removed by evaporation under reduced pressure. The mixture is diluted with water, made basic by addition of 2N aqueous potassium hydroxide solution and extracted with ethyl acetate (3×200 ml). The organic extracts are combined and the solvents are removed under reduced pressure to give 4′-chloro-3,5-diethylbiphen-4-ylamine (9.6 g).

Workup

customis removed by evaporation under reduced pressure
additionThe mixture is diluted with water
additionmade basic by addition of 2N aqueous potassium hydroxide solution
extractionextracted with ethyl acetate (3×200 ml)
customthe solvents are removed under reduced pressure

Sources & evidence

ORD record: ord-88d86efd347a4ea9ad9cf8574adee841
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08828908B2

Reaction notes

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