4,5-Dihydro-imidazo-[1,2-a]-quinoxaline-2-methanol → Imidazo-[1,2-a]quinoxaline-2-methanol

HRID 1632192Notes

Reaction equation

HRID 1632192 reaction equation
[CH:1]1[N:5]2[C:6]3[C:11]([NH:12][CH2:13][C:4]2=[N:3][C:2]=1[CH2:14][OH:15])=[CH:10][CH:9]=[CH:8][CH:7]=3>C(Cl)(Cl)Cl.[O-2].[O-2].[Mn+4]>[CH:1]1[N:5]2[C:6]3[C:11]([N:12]=[CH:13][C:4]2=[N:3][C:2]=1[CH2:14][OH:15])=[CH:10][CH:9]=[CH:8][CH:7]=3

Participants

4

Reactant 1

HCID 137704784,5-Dihydro-imidazo-[1,2-a]-quinoxaline-2-methanol

Product 1

HCID 13770472Imidazo-[1,2-a]quinoxaline-2-methanolYield 90.2%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6212ChloroformSolvent

Procedure

A solution of 3 g of 4,5-dihydro-imidazo-[1,2-a]-quinoxaline-2-methanol in 500 ml of chloroform and 9 g of manganese dioxide was refluxed with stirring for 6 hours and the mixture was filtered hot and concentrated. The mixuture was cooled and filtered to obtain 2.68 g of a imidazo-[1,2-a]-quinoxaline-2-methanol and imidazo-[1,2-a]-quinoxaline-2-carboxaldehyde mixture and the latter was chromatographed over silica gel. Elution with a 97.5% chloroform--2.5% methanol mixture yielded first 0.23 g of imidazo-[1,2-a]-quinoxaline-2-carboxaldehyde and then 1.42 g of imidazo-[1,2-a]-quinoxaline-2-methanol melting at 217°-220° C. Evaporation of the filtrate yielded 0.43 g of imidazo-[1,2-a]-quinoxaline-2-carboxaldehyde for a total yield of 0.66 g melting at 214°-215° C.

Workup

  1. filtrationthe mixture was filtered hot
  2. concentrationconcentrated
  3. temperatureThe mixuture was cooled
  4. filtrationfiltered

Sources & evidence

ORD record
ord-74324801229d4725bf4b6e49101b3184
Source dataset
uspto-grants-1984_10
Patent number
US04474784

Reaction notes

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