Nitric Acid → HCID 135838168, compound

HRID 1883997Notes

Reaction equation

HRID 1883997 reaction equation
[N+:1]([O-:4])(O)=[O:2].S(=O)(=O)(O)[OH:6].N[C:11]1[C:20]2[C:19]3[CH:21]=[CH:22][C:23]([Br:25])=[CH:24][C:18]=3[CH2:17][CH2:16][C:15]=2[N:14]=[C:13]([NH2:26])[N:12]=1>>[NH2:26][C:13]1[NH:12][C:11](=[O:6])[C:20]2[C:19]3[CH:21]=[C:22]([N+:1]([O-:4])=[O:2])[C:23]([Br:25])=[CH:24][C:18]=3[CH:17]=[CH:16][C:15]=2[N:14]=1

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 23507948HCID 23507948, compound

Product 1

HCID 135838168HCID 135838168, compound

Conditions

Temperature
2.5 °C

Procedure

To a mixture of fuming nitric acid (7 ml) and sulphuric acid (6 ml) at 0° C. was added 1,3-diamino-8-bromo-5,6-dihydrobenzo[f]quinazoline (1.0 g, 3.4 mmoles) in a single portion. The reaction mixture was stirred at 0-5° C. for 45 minutes, and then slowly poured onto ice (15 g). The resulting precipitate was filtered, washed with water (10 ml) and ether (10 ml), and resuspended in boiling 1N HCl (100 ml) for 1 hour. After cooling, the solid was filtered, triturated with hot ethanol, filtered again, washed with ethanol and ether, and dried to give 3-amino-8-bromo-9-nitrobenzo[f]quinazolin-1(2H)-one as a pale yellow solid. (0.59 g, 45%) 1H NMR (DMSO-d6, 80 MHz) δ: 7.62-7.71 (d, J=7 Hz, 1H, Ar); 7.77 (s, 3H, NH3+); 8.23-8.34 (d, J=9 Hz, 1H, Ar); 8.59 (s, 1H, Ar); 10.08 (s, 1H, Ar). Anal. Calculated for C12H7BrN4O3.1/2HNO3.H2O C, 37.47; H, 2.49; N, 16.39. Found C, 37.20; H, 2.24; N, 16.00.

Workup

  1. additionslowly poured onto ice (15 g)
  2. filtrationThe resulting precipitate was filtered
  3. washwashed with water (10 ml) and ether (10 ml)
  4. customfor 1 hour
  5. temperatureAfter cooling
  6. filtrationthe solid was filtered
  7. customtriturated with hot ethanol
  8. filtrationfiltered again
  9. washwashed with ethanol and ether
  10. customdried

Sources & evidence

ORD record
ord-72eae5fbeb7046c8b632beca7d1d73c8
Source dataset
uspto-grants-2004_07
Patent number
US06762188B1

Reaction notes

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