Nitric Acid → HCID 135838168, compound

HRID 381555Notes

Reaction equation

HRID 381555 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-7eaff0a1d4f84d7dad089ff4c3f35a52
Source dataset
uspto-grants-2001_10
Patent number
US06306865B1

Reaction notes

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