Hydrazine hydrate (1:1) → 3-(3-Bromo-5-chlorophenoxy)-2-hydrazino-4-methylpyridine

HRID 505567Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([CH:14]=[C:15]([Cl:17])[CH:16]=1)[O:5][C:6]1[C:7](Cl)=[N:8][CH:9]=[CH:10][C:11]=1[CH3:12].O.[NH2:19][NH2:20]>CS(C)=O>[Br:1][C:2]1[CH:3]=[C:4]([CH:14]=[C:15]([Cl:17])[CH:16]=1)[O:5][C:6]1[C:7]([NH:19][NH2:20])=[N:8][CH:9]=[CH:10][C:11]=1[CH3:12]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 3-(3-bromo-5-chlorophenoxy)-2-chloro-4-methylpyridine (121 mg, 0.363 mmol) in DMSO (1 mL) was added hydrazine hydrate (177 μL, 3.63 mmol) and the mixture was heated at 100° C. for 18 hours. The mixture was then purified on a Luna column (10μ, C18, 250×21.2 cm) eluting with 5-95% ACN/water with 0.1% TFA) to give the title compound. LRMS (M+1)=329.8.

Workup

customThe mixture was then purified on a Luna column (10μ, C18, 250×21.2 cm)
washeluting with 5-95% ACN/water with 0.1% TFA)

Sources & evidence

ORD record: ord-74fa4eb2ab544001a16aace5362289d0
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07781454B2

Reaction notes

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