Acetic Acid → HCID 59323905, compound

HRID 1715178Notes

Reaction equation

[N+]([CH:4]([CH3:17])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([N:12]2[CH:16]=[CH:15][CH:14]=[N:13]2)=[CH:8][CH:7]=1)([O-])=O.C(O)(=[O:20])C>[Fe]>[N:12]1([C:9]2[CH:10]=[CH:11][C:6]([CH2:5][C:4](=[O:20])[CH3:17])=[CH:7][CH:8]=2)[CH:16]=[CH:15][CH:14]=[N:13]1

Participants

Conditions

Temperature: 40 °C

Procedure

A stirred suspension comprising iron (10.7 g, 191.9 mmol) in glacial acetic acid (150 ml) under an inert atmosphere of argon is heated to 40° C. and then treated with a solution of 1-[4-(2-nitro-propyl)-phenyl]-1H-pyrazole (8.8 g, 38.39 mmol) in glacial acetic acid (100 ml). The reaction mixture is heated to 100° C. for 2 hours and then allowed to cool to room temperature. The mixture is poured onto ice-water (200 ml), stirred for 5 minutes and then filtered through celite washing through with DCM (50 ml). The organic portion of the filtrate is separated and the aqueous is extracted with DCM (150 ml). The organic portions are combined, washed with water (3×50 ml), brine (1×25 ml), dried (MgSO4) and concentrated in vacuo to afford the title compound as a red oil. [MH+ 201.25].

Workup

temperatureThe reaction mixture is heated to 100° C. for 2 hours
temperatureto cool to room temperature
additionThe mixture is poured onto ice-water (200 ml)
filtrationfiltered through celite
washwashing through with DCM (50 ml)
customThe organic portion of the filtrate is separated
extractionthe aqueous is extracted with DCM (150 ml)
washwashed with water (3×50 ml), brine (1×25 ml)
dry with materialdried (MgSO4)
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-ef58223ec3fe4b208c6f83c64779b0b7
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07799810B2

Reaction notes

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