1,4-Dioxane → HCID 18790636, compound

HRID 1107032Notes

Reaction equation

HRID 1107032 reaction equation
[O:1]=[C:2]1[NH:7][C:6]2[C:8]3[CH:9]=[CH:10][C:11]([CH2:15][C:16]([O:18]CC)=[O:17])=[CH:12][C:13]=3[CH2:14][C:5]=2[N:4]2[CH:21]=[CH:22][N:23]=[C:3]12.O1CCOCC1>Cl>[O:1]=[C:2]1[NH:7][C:6]2[C:8]3[CH:9]=[CH:10][C:11]([CH2:15][C:16]([OH:18])=[O:17])=[CH:12][C:13]=3[CH2:14][C:5]=2[N:4]2[CH:21]=[CH:22][N:23]=[C:3]12

Participants

4

Reactant 2

HCID 312751,4-DioxaneHCID 54131470HCID 54131470, compound

Product 1

HCID 18790636HCID 18790636, compoundYield 103.4%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A suspension of 0.5 g of ethyl [4,5-dihydro-4-oxo-10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-8-yl]acetate in 50 ml of 6N hydrochloric acid is heated at reflux for 2 hours. 25 ml of 1,4-dioxane are added to the mixture and reflux is continued for 4 hours. After returning to a temperature in the region of 20° C., the solid formed is filtered, washed with 5 ml of 1,4-dioxane and then dried under reduced pressure (1 mbar) at 60° C. 0.47 g of [4,5-dihydro-4-oxo-10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-8-yl]acetic acid is thus obtained in the form of a hydrochloride monohydrate, the melting point of which is greater than 260° C. (Analysis; % Calculated C: 56.7, H: 3.81, Cl: 11.16, N: 13.23; % Found C: 56.7, H: 3.9, Cl: 10.9, N: 12.9).

Workup

  1. temperatureis heated
  2. temperatureat reflux for 2 hours
  3. temperaturereflux
  4. customAfter returning to a temperature in the region of 20° C.
  5. customthe solid formed
  6. filtrationis filtered
  7. washwashed with 5 ml of 1,4-dioxane
  8. customdried under reduced pressure (1 mbar) at 60° C

Sources & evidence

ORD record
ord-f109cd84e0ee475fb0d5ad862809cd71
Source dataset
uspto-grants-2000_05
Patent number
US06057454

Reaction notes

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