Sodium Hydroxide → HCID 57901646, compound

HRID 1851351Notes

Reaction equation

HRID 1851351 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10]N=C(C(=O)CC)CC)([O-:3])=[O:2].[OH-:19].[Na+]>>[CH3:6][C:5]1[C:6]2[C:5](=[C:4]([N+:1]([O-:3])=[O:2])[CH:9]=[CH:8][CH:7]=2)[NH:10][C:4]=1[C:9](=[O:19])[CH2:8][CH3:7]

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 76636270HCID 76636270, compound

Product 1

HCID 57901646HCID 57901646, compoundYield 10%

Conditions

Temperature
80 °C

Procedure

A mixture of hexane-3,4-dione (2-nitrophenyl)hydrazone (3.13 g) and polyphosphoric acid (50 g) was stirred at 80° C. overnight. The reaction mixture was poured into ice water, neutralized with 50% aqueous sodium hydroxide solution, and extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography and the title compound (0.29 g, yield 10%) was obtained as yellow crystals from a fraction eluted with ethyl acetate-hexane (1:2, volume ratio). melting point>164° C. (decomposition).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-dc9d31023e7d4f61b242c53de01dbb92
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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