4-Nitrophenol → 4-(4-Nitrophenoxy)pyridin-2-amine

HRID 2265621Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.[N+:9]([C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1)([O-:11])=[O:10].C(N(CC)C(C)C)(C)C>CN1CCCC1=O>[NH2:1][C:2]1[CH:7]=[C:6]([O:18][C:15]2[CH:16]=[CH:17][C:12]([N+:9]([O-:11])=[O:10])=[CH:13][CH:14]=2)[CH:5]=[CH:4][N:3]=1

Participants

Conditions

Temperature: 150 °C

Procedure

2-Amino-4-chloropyridine (2.00 g) was dissolved in N-methylpyrrolidone (31.8 ml) under a nitrogen atmosphere, and 4-nitrophenol (6.51 g) and N,N-diisopropylethylamine (15.9 ml) were added, followed by stirring at 150° C. for 3 days. The reaction mixture was allowed to cool down to room temperature, and partitioned between ethyl acetate and a 1N aqueous solution of sodium hydroxide (32 ml). The organic layer was washed with water and brine in this order, and dried over anhydrous sodium sulfate. The solvent was concentrated under reduced pressure, and the resultant residue was purified by silica gel column chromatography (eluent; hexane:ethyl acetate=1:2 to 1:5). Fractions containing the target compound were concentrated under reduced pressure, and the residue was dried under reduced pressure to provide the titled compound as a brown solid (764 mg, 21.2%).

Workup

temperatureto cool down to room temperature
custompartitioned between ethyl acetate
washThe organic layer was washed with water and brine in this order
dry with materialdried over anhydrous sodium sulfate
concentrationThe solvent was concentrated under reduced pressure
customthe resultant residue was purified by silica gel column chromatography (eluent; hexane:ethyl acetate=1:2 to 1:5)
additionFractions containing the target compound
concentrationwere concentrated under reduced pressure
customthe residue was dried under reduced pressure

Sources & evidence

ORD record: ord-32efe75e75834f4ab69b3ed4bd5eeb8a
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07855290B2

Reaction notes

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