Methane → HCID 86753092, compound

HRID 2393422Notes

Reaction equation

HRID 2393422 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:6][C:7]3[N:12]4[CH:13]=[CH:14][N:15]=[C:11]4[C:10](=[O:16])[NH:9][C:8]=3[C:17]=2[CH:18]=1.C>CO>[ClH:1].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:6][C:7]3[N:12]4[CH:13]=[CH:14][N:15]=[C:11]4[C:10](=[O:16])[NH:9][C:8]=3[C:17]=2[CH:18]=1

Participants

4

Reactant 2

HCID 297MethaneHCID 18975471HCID 18975471, compound

Product 1

HCID 86753092HCID 86753092, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

7-Chloro-5H,10H-imidazo[1,2-a]indeno[1,2-e]-pyrazin-4-one may be prepared in the following way: 1 g of 1-[2-(6-chloro-1-oxoindanyl)]imidazole-2-carboxamide is dissolved in 50 ml of boiling methanol and, after addition of 0.1 g of decolorizing charcoal, the solution is filtered. The filter is washed with 25 ml of boiling methanol, then the filtrate and the washing are combined, 15 ml of aqueous 12N hydrochloric acid solution are added and the mixture is stored for 3 hours at 5° C. The crystals are isolated by filtration, washed twice with 20 ml in total of chilled methanol and dried under reduced pressure (1 mmHg; 0.13 kPa) at 60° C. 0.4 g of 7-chloro-5H,10H-imidazo-[1,2-a]indeno(1,2-e]pyrazin-4-one hydrochloride is thus obtained, decomposing without melting above 300° C. [NMR spectrum: (300 MHz; DMSO-d6 ; δ in ppm): 4.12 (s, 2H: --CH2 -- at 10); 7.44 (dd, J=8 and 1 Hz 1H: --H8); 7.66 (d, J=8 Hz, 1H: --H9); 7.95 and 8.25 (2 broad s, 1H each: --H of the imidazole); 8.05 (d, J=1 Hz, 1H: --H6); 12.97 (mult., 1H: --CONH--)].

Workup

  1. filtrationthe solution is filtered
  2. washThe filter is washed with 25 ml of boiling methanol
  3. addition15 ml of aqueous 12N hydrochloric acid solution are added
  4. customThe crystals are isolated by filtration
  5. washwashed twice with 20 ml in total of chilled methanol
  6. customdried under reduced pressure (1 mmHg; 0.13 kPa) at 60° C

Sources & evidence

ORD record
ord-58ac65e8e444470fbe15fd7799a5c96a
Source dataset
uspto-grants-1998_09
Patent number
US05807859

Reaction notes

Loading…