Sodium Bicarbonate → 3-Fluoro-4-(3-methyl-1H-1,2,4-triazol-1-YL)aniline

HRID 1452581Notes

Reaction equation

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

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 1-(2-Fluoro-4-nitro-phenyl)-3-methyl-1,2,4-triazole (Intermediate 28) (56.6 g, 0.255 mol) and SnCl22H2O (292 g, 1.29 mol) in ethanol (800 ml) was stirred at 70° C. under N2 for 1 hour. After cooling to room temperature, the reaction mixture was poured onto ice and the pH was made slightly basic by addition of NaHCO3 (solid) and extracted with ethyl acetate (3×). The combined organic phase was washed with brine (2×), dried over sodium sulfate and concentrated in vacuo to give the title compound as a colourless solid (48.8 g).

Workup

temperatureAfter cooling to room temperature
additionthe reaction mixture was poured onto ice
extractionextracted with ethyl acetate (3×)
washThe combined organic phase was washed with brine (2×)
dry with materialdried over sodium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-d867d3d8432c4145a4abb21671ea3b74
Source dataset: uspto-grants-2009_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07473699B2

Reaction notes

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