Ethanol → 2-(Benzyloxy)-4-{[5-(methylsulfonyl)pyridin-2-yl]oxy}aniline

HRID 1188917Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:23]=[CH:24][C:25]=1[N+:26]([O-])=O)[O:12][C:13]1[CH:18]=[CH:17][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:15][N:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[Ca+2].[Cl-].C(O)C>[Fe].O>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([O:12][C:13]2[CH:18]=[CH:17][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:15][N:14]=2)[CH:23]=[CH:24][C:25]=1[NH2:26])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 2-[3-(benzyloxy)-4-nitrophenoxy]-5-(methylsulfonyl)pyridine (45.56 g), iron powder (31.7 g), calcium chloride (1.26 g), ethanol (400 mL) and water (100 mL) was stirred at 80° C. for 3.5 h. The mixture was filtered through celite and the filtrate was concentrated. The residual solid was washed successively with water, ethanol, and diethyl ether to give the title compound (46.31 g, 100%) as a brownish-yellow solid. MS 371 (MH+).

Workup

filtrationThe mixture was filtered through celite
concentrationthe filtrate was concentrated
washThe residual solid was washed successively with water, ethanol, and diethyl ether

Sources & evidence

ORD record: ord-dc1a2d4b90424526bbce621c590a0ce2
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08673942B2

Reaction notes

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