Hydrochloric Acid → 3-[(2-Phenyl-6-pyridinyl)methoxy]benzenamine

HRID 330380Notes

Reaction equation

[N+:1]([C:4]1[CH:5]=[C:6]([CH:21]=[CH:22][CH:23]=1)[O:7][CH2:8][C:9]1[N:14]=[C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:12]=[CH:11][CH:10]=1)([O-])=O.Cl.[OH-].[NH4+]>O.C(OCC)(=O)C>[C:15]1([C:13]2[CH:12]=[CH:11][CH:10]=[C:9]([CH2:8][O:7][C:6]3[CH:5]=[C:4]([NH2:1])[CH:23]=[CH:22][CH:21]=3)[N:14]=2)[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A suspension of 6.2 g (0.02 mol) of 6-[(3-nitrophenoxy)methyl]-2-phenylpyridine in a solution of 50.0 g (0.18 mol) of ferrous sulfate heptahydrate and 0.3 ml of concentrated hydrochloric acid in 100 ml of water is heated on a steambath to 90° C. Concentrated ammonium hydroxide is added in 3 increments of 10 ml over a period of 10 minutes. Heating is discontinued and the reaction mixture is allowed to cool over a period of 45 minutes while vigorously stirring. The reaction mixture is diluted with 300 ml of water/300 ml of ethyl acetate and filtered through Celite. The filter cake is extracted once with 300 ml of ethyl acetate, and the combined ethyl acetate solution is concentrated in vacuo to obtain an oil (4.8 g). The oil is chromatographed with ethyl acetate/hexane as eluent. Fractions 8-11 are combined and concentrated to obtain 2.0 g (37%) of an oil, MS (CI) 277 (M+ H). The product is used without further purification in subsequent reactions.

Workup

temperatureHeating
temperatureto cool over a period of 45 minutes
filtrationfiltered through Celite
extractionThe filter cake is extracted once with 300 ml of ethyl acetate
concentrationthe combined ethyl acetate solution is concentrated in vacuo

Sources & evidence

ORD record: ord-26d82822749447d8aa8430e7f0948a93
Source dataset: uspto-grants-1990_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04895953

Reaction notes

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