Methanol → 4-(4-chloro-1H-imidazol-1-yl)-3-allyloxyaniline

HRID 474227Notes

Reaction equation

[CH2:1]([O:4][C:5]1[CH:10]=[C:9]([N+:11]([O-])=O)[CH:8]=[CH:7][C:6]=1[N:14]1[CH:18]=[C:17]([Cl:19])[N:16]=[CH:15]1)[CH:2]=[CH2:3].CO.[Cl-].[NH4+]>[Fe].O>[Cl:19][C:17]1[N:16]=[CH:15][N:14]([C:6]2[CH:7]=[CH:8][C:9]([NH2:11])=[CH:10][C:5]=2[O:4][CH2:1][CH:2]=[CH2:3])[CH:18]=1

Participants

Conditions

Temperature: 65 °C

Procedure

Iron powder-325 mesh (737 mg, 12.5 mmol) was added to a round bottom flask charged with a mixture of 1-(2-(allyloxy)-4-nitrophenyl)-4-chloro-1H-imidazole (500 mg, 1.8 mmol), absolute methanol (10 mL), and ammonium chloride (768 mg, 14 mmol). A water-cooled reflux condenser was attached to the flask and the heterogeneous mixture was heated to 65° C. with vigorous stirring for 30 min. The reaction mixture was filtered, and washed with methanol. The solvent was removed in vacuo. EtOAc was added to the residue, and washed with water and brine. The organic layer was dried over MgSO4, filtered, and concentrated to afford 4-(4-chloro-1H-imidazol-1-yl)-3-allyloxyaniline (380 mg, 83% yield). LC-MS (M+H)+250.0. 1H NMR (500 MHz, CDCl3) δ ppm 7.48 (d, J=1.22 Hz, 1H), 6.97-7.02 (m, 2H), 6.26-6.32 (m, 2H), 5.87-5.98 (m, 1H), 5.20-5.34 (m, 2H), 4.48 (d, J=5.19 Hz, 2H), 3.86 (br s, 2H).

Workup

temperaturereflux condenser
filtrationThe reaction mixture was filtered
washwashed with methanol
customThe solvent was removed in vacuo
additionEtOAc was added to the residue
washwashed with water and brine
dry with materialThe organic layer was dried over MgSO4
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-82e5e6481196416b89815be371cf7680
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08637523B2

Reaction notes

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