Stannous chloride dihydrate → 4-methoxy-3-(2-methyl-2H-pyrazol-3-yl)phenylamine

HRID 407412Notes

Reaction equation

HRID 407412 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-])=O)=[CH:5][C:4]=1[C:12]1[N:16]([CH3:17])[N:15]=[CH:14][CH:13]=1.O.O.Cl[Sn]Cl>CCO>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][C:4]=1[C:12]1[N:16]([CH3:17])[N:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 231395315-(2-Methoxy-5-nitrophenyl)-1-methyl-1H-pyrazole

Product 1

HCID 231394504-methoxy-3-(2-methyl-2H-pyrazol-3-yl)phenylamineYield 87%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5-(2-Methoxy-5-nitro-phenyl)-1-methyl-1H-pyrazole (2.11 g, 9.06 mmol) was treated with SnCl2.2H2O (8.341 g, 36.22 mmol, 4.0 equiv.) in EtOH (50 mL), in a similar manner as described in Example 1.1, providing 4-methoxy-3-(2-methyl-2H-pyrazol-3-yl)-phenylamine (1.592 g, 7.8 3 mmol, 87%) as an oil. LCMS m/z (%)=204 (M+H). 1H NMR (400 MHz, CDCl3) δ: 7.51 (d, J=1.8 Hz, 1H), 6.83 (d, J=8.7 Hz, 1H), 6.76 (dd, J=2.8, 8.7 Hz, 1H), 6.62 (d, J=2.8 Hz, 1H), 6.22 (d, J=1.8 Hz, 1H), 3.74 (s, 3H), 3.73 (s, 3H), 3.24-3.55 (broad s, 2H).

Sources & evidence

ORD record
ord-21bed424ae674ea99baea586984b8677
Source dataset
uspto-grants-2014_06
Patent number
US08754238B2

Reaction notes

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