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

HRID 341692Notes

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-6b86e18ac0a845a59725c0cdefaa9012
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08895761B2

Reaction notes

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