Sodium Hydroxide → [2-Methoxy-6-(2-methoxy-4-trifluoromethoxy-phenyl)-5-methyl-pyridin-3-yl]-hydrazine

HRID 2180001Notes

Reaction equation

[N:1]([O-])=O.[Na+].[CH3:5][O:6][C:7]1[C:12]([NH2:13])=[CH:11][C:10]([CH3:14])=[C:9]([C:15]2[CH:20]=[CH:19][C:18]([O:21][C:22]([F:25])([F:24])[F:23])=[CH:17][C:16]=2[O:26][CH3:27])[N:8]=1.Cl[Sn]Cl.[OH-].[Na+]>O.Cl.C(O)(=O)C>[CH3:5][O:6][C:7]1[C:12]([NH:13][NH2:1])=[CH:11][C:10]([CH3:14])=[C:9]([C:15]2[CH:20]=[CH:19][C:18]([O:21][C:22]([F:24])([F:25])[F:23])=[CH:17][C:16]=2[O:26][CH3:27])[N:8]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of NaNO2 (0.555 g, 8.04 mmol) in water (3 ml) is added to a stirred solution of 2-methoxy-6-(2-methoxy-4-trifluoromethoxy-phenyl)-5-methyl-pyridin-3-ylamine (2 g, 6.1 mmol) in concentrated HCl (3 ml), water (3 ml) and acetic acid (8 ml) below 0° C. over 20 minutes. The mixture is added to a stirred solution of SnCl2 2H2O (3.53 g, 15.7 mmol) in 4N HCl (9 ml) at 0° C. over 15 minutes. The mixture is stirred at 0° C. for 20 minutes and at room temperature for 30 minutes. The mixture is basified by NaOH solution at 0° C. and extracted with EtOAc. The combined extracts are dried over Na2SO4 and concentrated under reduced pressure to give [2-methoxy-6-(2-methoxy-4-trifluoromethoxy-phenyl)-5-methyl-pyridin-3-yl]-hydrazine. Rf (hexane/EtOAc=1:1)=0.24.

Workup

extractionextracted with EtOAc
dry with materialThe combined extracts are dried over Na2SO4
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-9e34bb628fd44de3b5ea867978e83210
Source dataset: uspto-grants-2005_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06887875B2

Reaction notes

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