Hydrochloric Acid → HCID 19691072, compound

HRID 1608Notes

Reaction equation

HRID 1608 reaction equation
C([N:3]1[C:8]2[C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=3[CH2:15][C:7]=2[N:6]2[C:16](Cl)=[C:17]([C:19]([O-:21])=[O:20])[N:18]=[C:5]2[C:4]1=[O:23])C.[ClH:24]>>[Cl:24][C:11]1[CH:12]=[CH:13][C:14]2[CH2:15][C:7]3[N:6]4[CH:16]=[C:17]([C:19]([OH:21])=[O:20])[N:18]=[C:5]4[C:4](=[O:23])[NH:3][C:8]=3[C:9]=2[CH:10]=1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 86752207HCID 86752207, compound

Product 1

HCID 19691072HCID 19691072, compound

Procedure

0.58 g of ethyl-chloro-4,5-dihydro-4-oxo-10H-imidazo[1,2-a]indeno[1,2-e]pyrazine-2-carboxylate in suspension in 10 ml of 6N hydrochloric acid is heated to reflux for 24 hours. After cooling to a temperature close to 20° C., the insoluble matter is filtered off, washed with water and dried under reduced pressure (1 mm Hg; 0.13 kPa) at 45° C. 0.38 g of 7-chloro-4,5-dihydro-4-oxo-10H-imidazo[1,2-a]indeno[1,2-e]-pyrazine-2-carboxylic acid is thus obtained in the form of a beige powder whose melting point is higher than 260° C. (analysis C14H10ClN3 O4 ; % calculated C: 52.60, H: 3.15, Cl: 11.09, N: 13.14; % found C: 52.9, H: 3.3, Cl: 10.8, N: 12.9); 1H spectrum in DMSO, T=300K, δ in ppm (300 MHz): 4.02 (2H, s, CH2), 7.37 (1H, d, J=7 Hz, CH arom.), 7.60 (1H, d, J=7 Hz, CH arom.), 7.92 (1H, s, CH arom.), 8.52 (1H, s, CH arom.), 12.45 (1H, s, NH)).

Workup

  1. temperatureto reflux for 24 hours
  2. temperatureAfter cooling to a temperature
  3. customclose to 20° C.
  4. filtrationthe insoluble matter is filtered off
  5. washwashed with water
  6. customdried under reduced pressure (1 mm Hg; 0.13 kPa) at 45° C

Sources & evidence

ORD record
ord-2183c14e46bb4ed985660d3128597a1a
Source dataset
uspto-grants-1998_03
Patent number
US05726175

Reaction notes

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