HCID 178467001, compound → HCID 178435013, compound

HRID 1729975Notes

Reaction equation

HRID 1729975 reaction equation
C([C:4]1[C:13]([CH2:14][O:15][CH:16]2[CH2:21]CCC[O:17]2)=[N+:12]([O-:22])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N+:5]=1[O-:23])(=O)C>C(O)(=O)C>[OH:17][C:16]1([CH3:21])[C:4]2=[N+:5]([O-:23])[C:6]3[C:11]([N+:12]([O-:22])=[C:13]2[CH2:14][O:15]1)=[CH:10][CH:9]=[CH:8][CH:7]=3

Participants

3

Reactant 1

HCID 178467001HCID 178467001, compound

Product 1

HCID 178435013HCID 178435013, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 0.578 g. (1.8 mmol.) of 2-acetyl-3-(2-tetrahydropyranyloxymethyl)quinoxaline 1,4-dioxide and 5.7 ml. of 40% aqueous acetic acid (prepared by mixing 40 parts of glacial acetic acid and 60 parts of water) was maintained at 40° C. for 3 hours. The solvents were removed by evaporation in vacuo. To the residue was added a small quantity of ethyl acetate, which was then removed by evaporation in vacuo. This procedure of adding ethyl acetate and then removing it by evaporation in vacuo was repeated several times. The residue was then washed with methyl isobutyl ketone, which finally afforded 0.354 g. (84% yield) of 1-hydroxy-1-methyl-1,3-dihydrofuro[3,4-b]quinoxaline 4,9-dioxide, m.p. 160°-162° C. (dec.).

Workup

  1. additionA mixture of 0.578 g
  2. customThe solvents were removed by evaporation in vacuo
  3. additionTo the residue was added a small quantity of ethyl acetate, which
  4. customwas then removed by evaporation in vacuo
  5. customThis procedure of adding ethyl acetate and then removing it
  6. customby evaporation in vacuo
  7. washThe residue was then washed with methyl isobutyl ketone, which finally afforded 0.354 g

Sources & evidence

ORD record
ord-a39f3a2aef4f440d963516d56a69e1e8
Source dataset
uspto-grants-1976_11
Patent number
US03991053

Reaction notes

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