Ammonium Hydroxide → HCID 135838174, compound

HRID 2289295Notes

Reaction equation

HRID 2289295 reaction equation
[NH2:1][C:2]1[N:11]=[C:10](N)[C:9]2[C:4](=[C:5]3[CH:20]=[CH:19][CH:18]=[CH:17][C:6]3=[C:7]3[CH:16]=[CH:15][CH:14]=[CH:13][C:8]3=2)[N:3]=1.[NH4+].[OH-:22]>Cl>[NH2:1][C:2]1[NH:11][C:10](=[O:22])[C:9]2[C:4](=[C:5]3[CH:20]=[CH:19][CH:18]=[CH:17][C:6]3=[C:7]3[CH:16]=[CH:15][CH:14]=[CH:13][C:8]3=2)[N:3]=1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 23507817HCID 23507817, compound

Product 1

HCID 135838174HCID 135838174, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A suspension of 2,4-diaminodibenzo[f,h]quinazoline (0.20 g, 0.76 mmol) in 1N HCl (150 ml) was stirred at reflux for 24 h, then neutralized with NH4OH. The resulting solid was filtered, washed with water and methanol, then suspended in warm methanol (50 ml) for 20 minutes, filtered and dried at 90° C. under reduced pressure. The solid was nearly dissolved in ethanol (100 ml) and 1N NaOH (~ 1.5 ml), filtered, and the filtrate neutralized with acetic acid to give a precipitate which was filtered, washed with ethanol, and dried at 90° C. under reduced pressure. The solid was briefly heated to reflux in pivalic anhydride (4 ml), the solution concentrated in vacuo, and the residue subjected to chromatography on silica gel, eluting with methylene chloride containing a small percentage of ethyl acetate. The pivalamide (not characterized) was hydrolyzed in a solution of methanol (9 ml) and 1N NaOH (1 ml) at reflux for 1.5 hours. The solution was neutralized with acetic acid, and the precipitate filtered, washed with methanol and dried at 90° C. under reduced pressure to give 2-aminodibenzo[f,h]quinazolin-4-(3H)-one as a beige solid (0.10 g). 1H NMR (DMSO-d6, 200 MHz) δ: 6.69 (br s, 2H, NH2), 7.47-7.84 (m, 4H, Ar), 8.66-8.80 (m, 2H, Ar), 8.96 (dd, J=8, 1 Hz, 1H, Ar), 9.75-9.83 (m, 1H, Ar), 11.26 (br s, 1H, NH). Mass spectrum (CI-CH4) 262 (M+1, 100%). Anal. Calculated for C16H11N3O: C, 73.55; H, 4.24; N, 16.08. Found: C, 73.52; H, 4.27; N, 16.03.

Workup

  1. temperatureat reflux for 24 h
  2. filtrationThe resulting solid was filtered
  3. washwashed with water and methanol
  4. filtrationfiltered
  5. customdried at 90° C. under reduced pressure
  6. dissolutionThe solid was nearly dissolved in ethanol (100 ml)
  7. filtration1N NaOH (~ 1.5 ml), filtered
  8. customto give a precipitate which
  9. filtrationwas filtered
  10. washwashed with ethanol
  11. customdried at 90° C. under reduced pressure
  12. temperatureThe solid was briefly heated
  13. temperatureto reflux in pivalic anhydride (4 ml)
  14. concentrationthe solution concentrated in vacuo
  15. washeluting with methylene chloride containing a small percentage of ethyl acetate
  16. temperatureat reflux for 1.5 hours
  17. filtrationthe precipitate filtered
  18. washwashed with methanol
  19. customdried at 90° C. under reduced pressure

Sources & evidence

ORD record
ord-8771fd851b9f4187a6690d865ac80bc4
Source dataset
uspto-grants-2000_07
Patent number
US06090941

Reaction notes

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