4-Methoxybenzaldehyde → 4(3H)-Quinazolinone, 2-(4-methoxyphenyl)-3,8-dimethyl-

HRID 2422572Notes

Reaction equation

HRID 2422572 reaction equation
[NH2:1][C:2]1[C:11]([CH3:12])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([NH:6][CH3:7])=[O:5].S([O-])(O)=O.[Na+].[CH:18](=O)[C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=1>>[CH3:26][O:25][C:22]1[CH:23]=[CH:24][C:19]([C:18]2[N:6]([CH3:7])[C:4](=[O:5])[C:3]3[C:2](=[C:11]([CH3:12])[CH:10]=[CH:9][CH:8]=3)[N:1]=2)=[CH:20][CH:21]=1

Participants

4

Reactant 3

HCID 312444-MethoxybenzaldehydeHCID 167706892-amino-N,3-dimethylbenzamideHCID 23665763Sodium Bisulfite

Product 1

HCID 672445924(3H)-Quinazolinone, 2-(4-methoxyphenyl)-3,8-dimethyl-Yield 49%

Conditions

Temperature
150 °C

Procedure

2-Amino-N,3-dimethylbenzamide (4.10 g, 25.0 mmol), sodium hydrogensulfite (2.93 g, 27.5 mmol) and para-anisaldehyde (3.4 g, 25 mmol) were mixed in N,N′-dimethylacetamide (20 ml), stirred at 150° C. for 5 hours, then cooled to room temperature, and distilled water (100 ml) was added thereto and stirred at that temperature for 1 hour. The precipitated solid was taken out through filtration, dried, and recrystallized from hot ethanol to obtain the intended compound (3.42 g, 49%) as a white solid.

Workup

  1. temperaturecooled to room temperature
  2. distillationdistilled water (100 ml)
  3. additionwas added
  4. stirringstirred at that temperature for 1 hour
  5. filtrationThe precipitated solid was taken out through filtration
  6. customdried
  7. customrecrystallized from hot ethanol

Sources & evidence

ORD record
ord-499f028cfe444e09b3f4c60eccd4acd4
Source dataset
uspto-grants-2011_06
Patent number
US07960394B2

Reaction notes

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