5-Chloro-2-nitroanisole → 5-Methyl-3-(3-methoxy-4-nitrophenyloxy)pyrazole

HRID 644830Notes

Reaction equation

HRID 644830 reaction equation
[OH:1][C:2]1[CH:6]=[C:5]([CH3:7])[NH:4][N:3]=1.Cl[C:9]1[CH:10]=[CH:11][C:12]([N+:17]([O-:19])=[O:18])=[C:13]([O:15][CH3:16])[CH:14]=1>>[CH3:7][C:5]1[NH:4][N:3]=[C:2]([O:1][C:9]2[CH:10]=[CH:11][C:12]([N+:17]([O-:19])=[O:18])=[C:13]([O:15][CH3:16])[CH:14]=2)[CH:6]=1

Participants

3

Reactant 2

HCID 811105-Chloro-2-nitroanisoleHCID 3197713H-Pyrazol-3-one, 2,4-dihydro-5-methyl-

Product 1

HCID 178623315-Methyl-3-(3-methoxy-4-nitrophenyloxy)pyrazoleYield 13.2%

Procedure

Reaction of 3-hydroxy-5-methylpyrazole with 5-chloro-2-nitroanisole was carried out in the same manner as Example 3, to give a yellow viscous substance of 5-methyl-3-(3-methoxy-4-nitrophenyloxy)pyrazole (yield: 13.2%). 1H-NMR (CDCl3, TMS, ppm): δ 2.34 (s, 3H), 3.93 (s, 3H), 5.74 (s, 1H), 6.70 (dd, J=2.4 and 9.1 Hz, 1H), 6.85 (d, J=2.4 Hz, 1H), 7.95 (d, J=9.1 Hz, 1H), 9.45 (br s, 1H).

Sources & evidence

ORD record
ord-55d4de3d0321412caa289c0ea8b8773c
Source dataset
uspto-grants-2010_04
Patent number
US07700786B2

Reaction notes

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