Glyoxal → HCID 87141418, compound

HRID 1662015Notes

Reaction equation

HRID 1662015 reaction equation
Cl.[F:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][NH2:10])=[CH:5][CH:4]=1.CCN(C(C)C)C(C)C.[CH:20](=O)[CH:21]=[O:22]>C1COCC1>[F:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9]/[N:10]=[CH:20]/[CH:21]=[O:22])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 7860GlyoxalHCID 699814-Fluorophenylhydrazine hydrochlorideHCID 81531Diisopropylethylamine

Product 1

HCID 87141418HCID 87141418, compoundYield 97.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 4-fluorophenylhydrazine hydrochloride (1 g, 6 mmol) in THF (20 mL) is treated with DIPEA (3 mL, 18 mmol). Then oxalaldehyde (40% in water, 0.89 g, 6.0 mmol) in THF (10 mL) is added dropwise in an ice-bath. After the addition, the mixture is stirred at RT for 30 min, quenched with water, and extracted with EtOAc. The organic phase is washed with saturated aqueous sodium chloride, dried over Na2SO4 and concentrated to afford the crude title compound (0.97 g, 97% yield). MS (m/z): 167 (M+H).

Workup

  1. additionAfter the addition
  2. customquenched with water
  3. extractionextracted with EtOAc
  4. washThe organic phase is washed with saturated aqueous sodium chloride
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b786b05ccc01466ca74f4563dc9de5b5
Source dataset
uspto-grants-2011_10
Patent number
US08030302B2

Reaction notes

Loading…