Water → HCID 87141418, compound

HRID 1676292Notes

Reaction equation

HRID 1676292 reaction equation
Cl.[F:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][NH2:10])=[CH:5][CH:4]=1.O.[CH:12]([CH:14]=O)=[O:13]>C(O)(=O)C>[F:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9]/[N:10]=[CH:14]/[CH:12]=[O:13])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 962WaterHCID 7860GlyoxalHCID 699814-Fluorophenylhydrazine hydrochloride

Product 1

HCID 87141418HCID 87141418, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 1-(4-fluorophenyl)hydrazine hydrochloride (5.0 g, 30.75 mmol), water (20 mL), and acetic acid (20 mL) was added with stirring to a 40% aqueous solution of glyoxal (17.6 mL, 153.8 mmol) over 20 minutes. Stirring was continued for 2 hours and then the mixture was filtered. The precipitate was washed with water and dried to afford 5.0 g (98%) of the desired product. 1H NMR (400 MHz, CDCl3) δ 9.56 (d, 1H), 8.63 (br s, 1H), 7.24 (m, 1H), 7.16 (m, 2H), 7.06 (m, 2H); 19F NMR (376 MHz, CDCl3) δ −120.3. LRMS (ESI pos) m/e 151.1 (M−16).

Workup

  1. additionwas added
  2. filtrationthe mixture was filtered
  3. washThe precipitate was washed with water
  4. customdried

Sources & evidence

ORD record
ord-db737a5b2885407a8afda81c5c71d2af
Source dataset
uspto-grants-2011_08
Patent number
US08003662B2

Reaction notes

Loading…