Water → 5-(2-Methoxy-4-nitrophenyl)oxazole

HRID 2230246Notes

Reaction equation

HRID 2230246 reaction equation
O.[CH3:2][O:3][C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:5]=1[C:13]1[O:17][CH:16]=[N:15][C:14]=1[C:18]([OH:20])=[O:19]>CN(C=O)C>[CH3:2][O:3][C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:5]=1[C:13]1[O:17][CH:16]=[N:15][C:14]=1[C:18]([OH:20])=[O:19].[CH3:2][O:3][C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:5]=1[C:13]1[O:17][CH:16]=[N:15][CH:14]=1

Participants

5

Reactant 2

HCID 962Water2×HCID 11323027HCID 11323027, compound

Product 2

HCID 101983405-(2-Methoxy-4-nitrophenyl)oxazoleHCID 11323027HCID 11323027, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

5-(2-Methoxy-4-nitrophenyl)-4-oxazolecarboxylic acid was prepared in the same manner as in Example 1-(1) and (2), and the resulting wet cake was dried. The dried product (13.2 g, 0.05 mol) was dissolved in 130 g of DMF. Water (66 g) was added thereto, and the solution was heated at 90° C. for 9 hours for decarboxylation. After cooling, 31 g of water was added to the reaction mixture. The mixture was stirred for 30 minutes, and the precipitate was collected by filtration to give 7.6 g (76% based on the 5-(2-methoxy-4-nitrophenyl)-4-oxazolecarboxylic acid) of the title compound as crystals.

Workup

  1. dry with material(2), and the resulting wet cake was dried
  2. temperatureAfter cooling
  3. filtrationthe precipitate was collected by filtration
  4. customto give 7.6 g (76%

Sources & evidence

ORD record
ord-15ccb324d25c43bb94cd1a2e59a709a1
Source dataset
uspto-grants-2002_07
Patent number
US06423849B1

Reaction notes

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