Methylglyoxal → HCID 87365555, compound

HRID 1676312Notes

Reaction equation

HRID 1676312 reaction equation
Cl.[F:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][NH2:10])=[CH:5][CH:4]=1.O.O=[C:13]([CH3:16])[CH:14]=[O:15]>C(O)(=O)C>[F:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9]/[N:10]=[C:13](\[CH3:16])/[CH:14]=[O:15])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 880MethylglyoxalHCID 962WaterHCID 699814-Fluorophenylhydrazine hydrochloride

Product 1

HCID 87365555HCID 87365555, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of (4-fluorophenyl)hydrazine HCl salt (2.0 g, 12.30 mmol), water (10 mL), and acetic acid (10 mL) was added with stirring to a 40% aqueous solution of 2-oxopropanal (9.41 mL, 61.5 mmol) for 20 minutes. Stirring was continued for 4 hours and the mixture was then filtered. The precipitate was washed with water and dried to afford the desired products. The crude was purified by silica gel flash column chromatography (1:50 to 1:10=EtOAc:CH2Cl2) to afford 2.05 g (93%) along with byproduct. 1H-NMR (400 MHz, CDCl3) δ 9.47 (s, 1H), 8.09 (br. s, 1H), 7.24 (m, 2H), 7.06 (t, 2H), 1.98 (s, 3H); 19F NMR (376 MHz, CDCl3) δ −121.0.

Workup

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

Sources & evidence

ORD record
ord-0a471d2d8b9b47d0a6e5e5086fee359a
Source dataset
uspto-grants-2011_08
Patent number
US08003662B2

Reaction notes

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