Ethanol → HCID 19979494, compound

HRID 1461806Notes

Reaction equation

HRID 1461806 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([CH2:7][N:8]2[C:13]3[CH:14]=[CH:15][C:16]([N+:18]([O-])=O)=[CH:17][C:12]=3[O:11][CH2:10][C:9]2=[O:21])[N:3]=1.C(O)C.[OH-].[K+]>Cl>[NH2:18][C:16]1[CH:15]=[CH:14][C:13]2[N:8]([CH2:7][C:4]3[N:3]=[C:2]([CH3:1])[O:6][N:5]=3)[C:9](=[O:21])[CH2:10][O:11][C:12]=2[CH:17]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 19979495HCID 19979495, compound

Product 1

HCID 19979494HCID 19979494, compoundYield 38.3%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of 4-(5-methyl-1,2,4-oxadiazol-3-ylmethyl)-7-nitro-2H-1,4-benzoxazin-3(4H)-one (3.2 g) and ethanol (40 ml) was prepared. To this mixture was added a solution of stannous chloride dihydrate (11.3 g) in concentrated hydrochloric acid (44 ml) at a temperature of 10° to 20° C. The reaction mixture was stirred at a temperature of 60° to 70° C., and distilled to dryness under a reduced pressure. The resulting residue was admixed with ice (150 g). To the mixture thus obtained was added dropwise a 25% aqueous potassium hydroxide solution at a temperature of 0° to 10° C. to render the mixture alkaline. The resultant alkaline solution was extracted with dichloromethane (80 ml×2). The dichloromethane layer was washed with water, and dried over anhydrous sodium sulfate. The dichloromethane solvent was distilled off under a reduced pressure, and the resultant solid residue (1.3 g) was recrystallized from toluene, so that the aimed compound, i.e. 7-amino-4-(5-methyl-1,2,4-oxadiazol-3-ylmethyl)-2H-1,4-benzoxazin-3(4H)-one (1.1 g) was obtained. m.p. 146°-147.5° C.

Workup

  1. customwas prepared
  2. distillationdistilled to dryness under a reduced pressure
  3. customTo the mixture thus obtained
  4. extractionThe resultant alkaline solution was extracted with dichloromethane (80 ml×2)
  5. washThe dichloromethane layer was washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationThe dichloromethane solvent was distilled off under a reduced pressure
  8. customthe resultant solid residue (1.3 g) was recrystallized from toluene, so that the aimed compound

Sources & evidence

ORD record
ord-9a1dcdf9faf44e7db32a29fde3fe71ae
Source dataset
uspto-grants-1991_12
Patent number
US05077401

Reaction notes

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