Hydrochloric Acid → (2-Amino-5-chloro-phenyl)-(3-methyl-[1,2,3]triazol-4-yl)methanone

HRID 29514Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N+:16]([O-])=O)=[C:6]([C:8]([C:10]2[N:11]([CH3:15])[N:12]=[N:13][CH:14]=2)=[O:9])[CH:7]=1.Cl>CO>[NH2:16][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][C:6]=1[C:8]([C:10]1[N:11]([CH3:15])[N:12]=[N:13][CH:14]=1)=[O:9]

Participants

Conditions

Temperature: 100 °C

Procedure

To 31 mg (0.12 mmol) of (5-Chloro-2-nitro-phenyl)-(3-methyl-[1,2,3]triazol4-yl)-methanone in 1.5 ml of methanol were added 0.05 ml of 12M HCl and 200 mg (0.89 mmol) of stannous (II) chloride monohydrate, and the mixture was heated at 100° C. for four hours. The mixture was then cooled to ambient temperature, partitioned between 1M NaOH and ethyl acetate, and the phases were separated. The ethyl acetate phase was washed once each with water and brine, dried over Na2SO4, filtered, and concentrated in vacuo to a solid. The solid was chromatographed to give the title product as a yellow solid.

Workup

temperatureThe mixture was then cooled to ambient temperature
custompartitioned between 1M NaOH and ethyl acetate
customthe phases were separated
washThe ethyl acetate phase was washed once each with water and brine
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo to a solid
customThe solid was chromatographed

Sources & evidence

ORD record: ord-6cd8dae7c2f1486ebbe76a747f80cb2b
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07420055B2

Reaction notes

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