Dimethylformamide → HCID 75061513, compound

HRID 2239035Notes

Reaction equation

HRID 2239035 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][N:9]=[C:10]([CH3:16])[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:4]([N+:17]([O-:19])=[O:18])[CH:3]=1.CI.[C:22](=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH3:22][O:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][N:9]=[C:10]([CH3:16])[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:4]([N+:17]([O-:19])=[O:18])[CH:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 76540792HCID 76540792, compound

Product 1

HCID 75061513HCID 75061513, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of ethyl 2-[(4-hydroxy-2-nitrophenyl)hydrazono]propanoate (30 g), methyl iodide (21.3 g), potassium carbonate (21 g) and N,N-dimethylformamide (300 mL) was stirred at room temperature for 2 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with 1N hydrochloric acid and saturated brine, dried (MgSO4), and concentrated. The obtained residue was crystallized from diethyl ether to give the title compound (28 g, yield 89%) as orange crystals. MS: 282 (MH+).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with 1N hydrochloric acid and saturated brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe obtained residue was crystallized from diethyl ether

Sources & evidence

ORD record
ord-afb7b5065d114c7a902a98d9f8eb7f1d
Source dataset
uspto-grants-2010_05
Patent number
US07718798B2

Reaction notes

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