Ammonia → HCID 18918197, compound

HRID 1290772Notes

Reaction equation

HRID 1290772 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6](=[N:19]O)[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([O-])(=[O:23])C.[NH4+].N.[ClH:27]>C(O)C.[Zn]>[OH2:16].[OH2:23].[OH2:16].[ClH:1].[ClH:27].[NH2:19][CH:6]1[C:7]2[N:12]3[CH:13]=[CH:14][N:15]=[C:11]3[C:10](=[O:16])[NH:9][C:8]=2[C:17]2[CH:18]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]1=2

Participants

7

Reactant 4

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 517165Ammonium AcetateHCID 178518652HCID 178518652, compound

Product 1

HCID 18918197HCID 18918197, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 702EthanolSolvent

Procedure

To a suspension of 1.05 g of 7-chloro-10-hydroxyimino-5H,10H-imidazo[1,2-a]indeno[1,2-e]-pyrazin-4-one in 35 ml of ethanol in the presence of 0.12 g of ammonium acetate and 35 ml of 28% aqueous ammonia are progressively added 1.07 g of zinc powder. The reaction mixture is brought to reflux for 5 hours. After cooling to a temperature in the region of 20° C., 45 ml of 6N hydrochloric acid are added dropwise to the reaction medium and stirring is continued for 24 hours at the same temperature. The precipitate formed is filtered off, washed with water and dried under reduced pressure (1 mmHg; 0.13 kPa) at 50° C. 0.35 g of 10-amino-7-chloro-5H,10H-imidazo[1,2-a]indeno[1,2-e]-pyrazin-4-one dihydrochloride trihydrate is thus obtained, in the form of a beige powder decomposing at 250° C. [N.M.R. spectrum: (250 MHz; DMSO d6 ; δ in ppm): 5.70 (broad s, 1H: CH at 10); (dd, J=8 and 2 Hz, 1H: H-8); 7.67 and 8.57 (2d, J=1 Hz, 1H each: H of the imidazole); 8.01 (d, J=2 Hz, 1H: H-6); 8.01 (d, J=8 Hz, 1H: H-9); 9.30 (cplx, 1H: NH2) 12.70 (cplx, 1H: CONH)].

Workup

  1. temperatureto reflux for 5 hours
  2. additionare added dropwise to the reaction medium
  3. customThe precipitate formed
  4. filtrationis filtered off
  5. washwashed with water
  6. customdried under reduced pressure (1 mmHg; 0.13 kPa) at 50° C

Sources & evidence

ORD record
ord-3a5120bdfd0040e3a0563fe4e0fc8cd8
Source dataset
uspto-grants-1998_05
Patent number
US05753657

Reaction notes

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