Hydrochloric Acid → HCID 68553173, compound

HRID 2381941Notes

Reaction equation

HRID 2381941 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:9][N:10]([NH:15]C(=O)C)[C:11](=[O:14])[NH:12][N:13]=2)=[CH:4][CH:3]=1.Cl.[OH-].[Na+]>CO>[NH2:15][N:10]1[CH2:9][C:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)=[N:13][NH:12][C:11]1=[O:14]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 68557332HCID 68557332, compound

Product 1

HCID 68553173HCID 68553173, compoundYield 88.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a slurry of N-[6-(4-fluoro-phenyl)-3-oxo-2,5-dihydro-3H-1,2,4-triazin-4-yl]-acetamide (0.48 g, 1.9 mmol) in MeOH (5 mL) is added 37% aqueous HCl. The mixture is heated to reflux for 3 h, and then cooled to rt. The mixture is basified with 1 M aqueous NaOH to pH ˜12. The resulting precipitate is collected by filtration and dried to afford 4-amino-6-(4-fluoro-phenyl)-4,5-dihydro-2H-1,2,4-triazin-3-one (0.35 g, 88%). MS: 209 (M+H); 1H NMR (300 MHz, DMSO-d6) δ 10.17 (s, 1H), 7.67-7.75 (m, 2H), 7.18-7.29 (m, 2H), 4.75 (s, 2H), 4.45 (s, 2H).

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux for 3 h
  3. filtrationThe resulting precipitate is collected by filtration
  4. customdried

Sources & evidence

ORD record
ord-02e4b79e610a4e09b312c554ada66325
Source dataset
uspto-grants-2012_09
Patent number
US08258130B2

Reaction notes

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