Sulfuric Acid → HCID 70084284, compound

HRID 1489028Notes

Reaction equation

HRID 1489028 reaction equation
[Br:1][C:2]1[C:3]2[CH2:4][C:5]3[N:10]4[CH:11]=[CH:12][N:13]=[C:9]4[C:8](=[O:14])[NH:7][C:6]=3[C:15]=2[CH:16]=[CH:17][CH:18]=1.S(=O)(=O)(O)O.[N+:24]([O-])([O-:26])=[O:25].[K+]>>[N+:24]([C:18]1[CH:17]=[CH:16][C:15]2[C:6]3[NH:7][C:8](=[O:14])[C:9]4[N:10]([CH:11]=[CH:12][N:13]=4)[C:5]=3[CH2:4][C:3]=2[C:2]=1[Br:1])([O-:26])=[O:25]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 24434Potassium NitrateHCID 67622829HCID 67622829, compound

Product 1

HCID 70084284HCID 70084284, compoundYield 74.8%

Conditions

Temperature
20 °C

Procedure

1 g of 9-bromo-5H, 10H-imidazo[1,2-a]indeno-[1,2-e]pyrazin-4-one is added to 6 ml of concentrated sulphuric acid (20N) at a temperature close to 0° C. 0.3 g of potassium nitrate is then added in two portions to this solution while maintaining the temperature between 0° and 5° C. The reaction medium is stirred for 18 hours at 20° C., then poured into 50 ml of ice-cold water. The insoluble matter is filtered, washed with 50 ml of ethyl acetate and dried under reduced pressure (15 mmHg; 2 kPa) at 50° C. 0.77 g of 8-nitro-9-bromo-5H, 10H-imidazo[1,2-a]indeno[1,2-e]-pyrazin-4-one is thus obtained which melts above 260° C. (analysis: % calculated C: 44.98, H: 2.03, Br: 23.02, N: 16.14, % found C: 45.40, H: 2.20, Br: 21.30, N: 15.70).

Workup

  1. customclose to 0° C
  2. temperaturewhile maintaining the temperature between 0° and 5° C
  3. filtrationThe insoluble matter is filtered
  4. washwashed with 50 ml of ethyl acetate
  5. customdried under reduced pressure (15 mmHg; 2 kPa) at 50° C

Sources & evidence

ORD record
ord-f621bc6600184d43b82591215b4c7230
Source dataset
uspto-grants-1997_10
Patent number
US05677306

Reaction notes

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