Ammonia → 6-Methoxy-2-methylquinazoline

HRID 2404186Notes

Reaction equation

HRID 2404186 reaction equation
F[C:2](F)([CH2:6][NH:7][CH2:8][C:9]1[CH:18]=[CH:17][C:16]2[C:11](=CC=C(OC3CCC4(CCCCC4)CC3)C=2)[CH:10]=1)C(O)=O.[NH3:32].[CH2:33]([OH:35])C>>[CH3:33][O:35][C:11]1[CH:10]=[C:9]2[C:18](=[CH:17][CH:16]=1)[N:32]=[C:6]([CH3:2])[N:7]=[CH:8]2

Participants

4

Reactant 3

HCID 222AmmoniaHCID 702Ethanol2×HCID 66926364HCID 66926364, compound

Product 1

HCID 545782166-Methoxy-2-methylquinazoline

Conditions

Temperature
-78 °C

Procedure

N-(2-Formyl-4-methoxyphenyl)acetamide (2, 2.50 g, 12.9 mmol) was dissolved in Ethanol (300 mL, 5000 mmol) and cooled to at −78° C. in a high pressure reactor. A solution of NH3 saturated in ethanol was added. The reaction mixture was then heated at 135° C. for 2 hours. Cooled to 23° C., and solvent was removed to give a crude product, which was then purified via chromatography (SiO2, 120 g, 0-20% MeOH/DCM; 1.87 g, 83%). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 2.91 (s, 3H) 3.97 (s, 3H) 7.15 (d, J=2.51 Hz, 1H) 7.56 (dd, J=9.04, 2.51 Hz, 1H) 7.93 (d, J=9.04 Hz, 1H) 9.27 (s, 1H). MS (ESI, M+1): 175.10.

Workup

  1. temperatureThe reaction mixture was then heated at 135° C. for 2 hours
  2. temperatureCooled to 23° C.
  3. customsolvent was removed

Sources & evidence

ORD record
ord-25c93c87a47849fea740d285d90aa238
Source dataset
uspto-grants-2014_08
Patent number
US08802659B2

Reaction notes

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