Ammonium Hydroxide → HCID 86677067, compound

HRID 1520309Notes

Reaction equation

HRID 1520309 reaction equation
P(Cl)(Cl)([Cl:3])=O.[CH3:6][O:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[N:14]=[C:13]([C:18]1[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=1)[NH:12][C:11]2=O.[OH-].[NH4+]>>[Cl:3][C:11]1[C:10]2[C:15](=[CH:16][CH:17]=[C:8]([O:7][CH3:6])[CH:9]=2)[N:14]=[C:13]([C:18]2[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=2)[N:12]=1

Participants

4

Reactant 3

HCID 14923Ammonium HydroxideHCID 24813Phosphorus oxychlorideHCID 135999593HCID 135999593, compound

Product 1

HCID 86677067HCID 86677067, compoundYield 88.1%

Conditions

Temperature
120 °C

Procedure

In a sealed tube, phosphorus oxychloride (11 mL, 120 mmol) was added to 6-methoxy-2-(pyridin-3-yl)quinazolin-4(3H)-one (2.70 g, 10.66 mmol). The mixture was refluxed at 120° C. for 12 h. After cooling, the remaining phosphorus oxychloride was removed in vacuo to leave a tan solid. This residue was added to an ice-water mixture (100 mL) with cooling and allowed to stir. The pH of the suspension was adjusted to about pH 9 via dropwise addition of 28% ammonium hydroxide, and stirring was continued for 30 mins. The resulting solid was filtered to give the desired product as a tan solid (2.55 g, 9.39 mmol, 88%). LC-MS m/z=272.0 (M+1) (retention time=2.05) 1H NMR (300 MHz, DMSO) δ 9.55 (s, 1H), 8.81-8.64 (m, 2H), 8.09 (d, J=9.2 Hz, 1H), 7.78 (dd, J=9.2, 2.8 Hz, 1H), 7.61 (dd, J=7.9, 4.8 Hz, 1H), 7.49 (d, J=2.5 Hz, 1H), 4.00 (s, 3H).

Workup

  1. temperatureAfter cooling
  2. customthe remaining phosphorus oxychloride was removed in vacuo
  3. customto leave a tan solid
  4. temperaturewith cooling
  5. stirringstirring
  6. filtrationThe resulting solid was filtered

Sources & evidence

ORD record
ord-8acbd92a16234e9292f7c2ea164be379
Source dataset
uspto-grants-2015_07
Patent number
US09073890B2

Reaction notes

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