Hydrochloric Acid → 2-(2-(2-Bromo-5-fluorophenyl)hydrazono)acetic acid

HRID 1664176Notes

Reaction equation

HRID 1664176 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[NH:9][NH2:10].Cl.O.[C:13]([OH:17])(=[O:16])[CH:14]=O>O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[NH:9][N:10]=[CH:14][C:13]([OH:17])=[O:16]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 12891829(2-Bromo-5-fluorophenyl)hydrazineHCID 15620607Glyoxylic acid, monohydrate

Product 1

HCID 674393932-(2-(2-Bromo-5-fluorophenyl)hydrazono)acetic acidYield 98%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of (2-bromo-5-fluorophenyl)hydrazine (2.15 g, 10.5 mmol) and concentrated HCl (1.2 mL) in water (30 mL) was added glyoxylic acid hydrate (1.06 g, 11.5 mmol). The resulting mixture was stirred at room temperature for 2 h. The precipitate that formed was collected by filtration, washed with water and dried at reduced pressure to afford the title compound as a yellow solid (2.67 g, 98% yield): 1H NMR (400 MHz, DMSO-D6) δ ppm 12.57 (1H, s), 10.65 (1H, s), 7.65 (1H, s), 7.56 (1H, dd, J=8.7, 5.9 Hz), 7.31 (1H, dd, J=11.4, 3.0 Hz), 6.73 (1H, td, J=8.5, 3.0 Hz); LCMS (+ESI, M+H+) m/z 261-263.

Workup

  1. customThe precipitate that formed
  2. filtrationwas collected by filtration
  3. washwashed with water
  4. customdried at reduced pressure

Sources & evidence

ORD record
ord-8634b664e8e3422e91f71b2dfc71069d
Source dataset
uspto-grants-2011_10
Patent number
US08039458B2

Reaction notes

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