Glyoxal → HCID 87141418, compound

HRID 2195531Notes

Reaction equation

HRID 2195531 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-3ba9d7239ba94030993edb7978fd99ac
Source dataset
uspto-grants-2012_12
Patent number
USRE043878E1

Reaction notes

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