Water → HCID 178418245, compound

HRID 1607

Reaction equation

HRID 1607 reaction equation
[H-].[Na+].[O:3]=[C:4]1[NH:9][C:8]2[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=3[CH2:16][C:7]=2[N:6]2[CH:17]=[C:18]([C:20]([O:22]CC)=[O:21])[N:19]=[C:5]12.[N:25](OCCC(C)C)=[O:26].O>CS(C)=O.C(O)(=O)C>[OH:26][N:25]=[C:16]1[C:7]2[N:6]3[CH:17]=[C:18]([C:20]([OH:22])=[O:21])[N:19]=[C:5]3[C:4](=[O:3])[NH:9][C:8]=2[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:15]1=2

Participants

7

Reactant 4

HCID 962WaterHCID 8053Isoamyl NitriteHCID 24758Sodium hydrideHCID 19691063ethyl 4,5-dihydro-4-oxo-10H-imidazo[1,2-a]indeno[1,2-e]pyrazine-2-carboxylate

Product 1

HCID 178418245HCID 178418245, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 679Dimethyl SulfoxideSolvent

Procedure

0.34 g of sodium hydride is added to 1 g of ethyl 4,5-dihydro-4-oxo-10H-imidazo[1,2-a]indeno[1,2-e]pyrazine-2-carboxylate in solution in 20 ml of anhydrous dimethyl sulphoxide, while the temperature of the reaction mixture is maintained below 20° C. 0.44 ml of isoamyl nitrite is then added and stirring is continued for 18 hours at the same temperature. The reaction mixture is then poured into iced water and the solution is acidified with 15 ml of acetic acid. The precipitate formed is filtered off, washed with water, with acetone and then with methanol and finally dried under reduced pressure (1 mm Hg; 0.13 kPa) to produce 0.25 g of 10-hydroxyimino-4,5-dihydro-4-oxo-imidazo[1,2-a]indeno[1,2-e]pyrazine-2-carboxylic acid in the form of a brown powder whose melting point is higher than 260° C. (1H spectrum in DMSO, T=300K, δ in ppm (200 MHz), mixture of the syn and anti isomers: Major isomer: between 7.30 and 7.50 (2H, m, CH arom.), 7.62 (1H, s, CH arom.), 7.82 (1H, d, J=7 Hz, CH arom.), 8.00 (1H, s, CH arom.), 8.20 (1H, d, J=7 Hz, CH arom.), 12.7 (1H, s, NH), 13.0 (1H, s, OH), Minor isomer: between 7.30 and 7.50 (2H, m, CH arom.), 7.51 (1H, s, CH arom.), 7.70 (1H, d, J=7 Hz, CH arom.), 7.88 (1H, d, J=7 Hz, CH arom.), 8.58 (1H, s, CH arom.), 12.7 (1H, s, NH), 13.2 (1H, s, OH)).

Workup

  1. temperatureis maintained below 20° C
  2. customThe precipitate formed
  3. filtrationis filtered off
  4. washwashed with water, with acetone
  5. dry with materialwith methanol and finally dried under reduced pressure (1 mm Hg; 0.13 kPa)

Sources & evidence

ORD record
ord-71deb639e501406b8994cac9a143516e
Source dataset
uspto-grants-1998_03
Patent number
US05726175

Linked notes

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