Methane → HCID 9859557, compound

HRID 1290739Notes

Reaction equation

HRID 1290739 reaction equation
[BH4-].[Na+].[CH:3]1[N:7]2[C:8]3[C:19](=[O:20])[C:18]4[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=4[C:9]=3[NH:10][C:11](=[O:12])[C:6]2=[N:5][CH:4]=1.C>CO.CN(C)C=O>[OH:20][CH:19]1[C:8]2[N:7]3[CH:3]=[CH:4][N:5]=[C:6]3[C:11](=[O:12])[NH:10][C:9]=2[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:18]1=2

Participants

6

Reactant 3

HCID 297MethaneHCID 4311764Sodium borohydrideHCID 15291360HCID 15291360, compound

Product 1

HCID 9859557HCID 9859557, compoundYield 78.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
20 °C

Procedure

0.86 g of sodium borohydride is added over 5 minutes to a stirred suspension of 2.4 g of 5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazine-4,10-dione in 75 ml of methanol at a temperature between 25° C. and 35° C. After stirring for 30 minutes at 20° C., the insoluble material is isolated by filtration, washed with 10 ml of methanol and dried under reduced pressure (15 mmHg; 2 kPa) at 20° C. The product obtained (2.3 g) is dissolved in 100 ml of dimethylformamide and, after addition of 0.1 g of decolorizing charcoal, the solution is filtered and the filter is then washed with 20 ml of dimethylformamide. The filtrate and the washings are combined and 240 ml of distilled water are added. The solid is filtered off, washed twice with 40 ml in total of distilled water and with 20 ml of acetone and then dried under reduced pressure (1 mmHg; 0.13 kPa) at 100° C. 1.9 g of 10-hydroxy-5H,10H-imidazo-[1,2-a]indeno[1,2-e]pyrazin-4-one are thus obtained, melting at 290° C. (decomposition) [N.M.R. spectrum: (200 MHz; DMSO d6 ; δ in ppm): 5.65 (d, J=8.5 Hz, 1H: CH--O--); 6.17 (d, J=8.5 Hz, 1H: --OH); 7.33 and 7.41 (2dt, J=7.5 and 1 Hz, 1H each: --H7 and --H8); 7.57 and 7.77 (2dd, J=7.5 and 1 Hz, 1H each: --H6 and --H9); 7.58 and 7.93 (2s broad, 1H each: --H of the imidazole); 12.40 (cplx, 1H: --NH--)].

Workup

  1. customthe insoluble material is isolated by filtration
  2. washwashed with 10 ml of methanol
  3. customdried under reduced pressure (15 mmHg; 2 kPa) at 20° C
  4. customThe product obtained (2.3 g)
  5. filtrationthe solution is filtered
  6. washthe filter is then washed with 20 ml of dimethylformamide
  7. addition240 ml of distilled water are added
  8. filtrationThe solid is filtered off
  9. washwashed twice with 40 ml in total of distilled water and with 20 ml of acetone
  10. customdried under reduced pressure (1 mmHg; 0.13 kPa) at 100° C

Sources & evidence

ORD record
ord-9d98c349584d471cbe123f4d88ef3b0c
Source dataset
uspto-grants-1998_05
Patent number
US05753657

Reaction notes

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