4-Aminophenol → 4-(3,5-Dichloro-pyridin-4-yloxy)-phenylamine

HRID 1433131Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.CC([O-])(C)C.[K+].[Cl:15][C:16]1[CH:17]=[N:18][CH:19]=[C:20]([Cl:23])[C:21]=1Cl>CN(C=O)C.C(OCC)(=O)C>[Cl:15][C:16]1[CH:17]=[N:18][CH:19]=[C:20]([Cl:23])[C:21]=1[O:8][C:5]1[CH:6]=[CH:7][C:2]([NH2:1])=[CH:3][CH:4]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a vial containing 4-aminophenol (2.185 g, 20.0 mmol, 1 equiv.) in 60 mL DMF was added t-BuOK (2.468 g, 22.0 mmol, 1.1 equiv.) followed by 3,4,5-trichloropyridine (3.653 g, 20.0 mmol, 1 equiv.). The flask was fitted with a condenser and the mixture was stirred at 80° C. under nitrogen. After the reaction mixture was cooled, diluted with ethyl acetate (600 mL) and washed with water (3×150 mL) and brine. The organic layer was dried over Na2SO4, filtered and solvent was removed under vacuum. The crude material was absorbed onto silica gel and purified by flash column (7.5×12 cm silica) using 2500 mL 1:1 hexanes:ethyl acetate giving 4.6348 g (91%) of product as a light yellow crystalline solid.

Workup

customThe flask was fitted with a condenser
temperatureAfter the reaction mixture was cooled
washwashed with water (3×150 mL) and brine
dry with materialThe organic layer was dried over Na2SO4
filtrationfiltered
customsolvent was removed under vacuum
customThe crude material was absorbed onto silica gel
custompurified by flash column (7.5×12 cm silica)

Sources & evidence

ORD record: ord-188c11633e3343aabecdfa21d5ec7e55
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07612200B2

Reaction notes

Loading…