2-Methylbenzaldehyde → HCID 135907957, compound

HRID 555565Notes

Reaction equation

HRID 555565 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[C:7]([O:13][CH3:14])[C:3]=1[C:4]([NH2:6])=[O:5].[CH3:15][C:16]1[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=1[CH:18]=O.OS([O-])=O.[Na+].CC1C=CC(S(O)(=O)=O)=CC=1.O>CC(N(C)C)=O.CCOC(C)=O.O>[CH3:14][O:13][C:7]1[CH:8]=[C:9]([O:11][CH3:12])[CH:10]=[C:2]2[C:3]=1[C:4](=[O:5])[NH:6][C:15]([C:16]1[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=1[CH3:18])=[N:1]2

Participants

8

Reactant 4

HCID 107222-MethylbenzaldehydeHCID 521998p-Toluenesulfonic acid monohydrateHCID 203490162-Amino-4,6-dimethoxybenzamideHCID 23665763Sodium Bisulfite

Product 1

HCID 135907957HCID 135907957, compoundYield 28%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 2-amino-4,6-dimethoxybenzamide (0.060 g, 0.306 mmol), 2-methylbenzaldehyde (0.037 g, 0.306 mmol), NaHSO3 (0.032 g, 0.306 mmol), and p-TsOH.H2O (0.00370 g, 0.021 mmol) in DMA (5.00 mL) was heated at 60° C. overnight. The mixture was cooled to room temperature, water (50.0 mL) and EtOAc (50.0 mL) was added. The layers were separated and the organic layer was washed with water (2×50 mL), brine (50 mL), dried and concentrated. The crude solid was purified via CombiFlash provide 5,7-dimethoxy-2-o-tolylquinazolin-4(3H)-one (0.025 g, 28%) as yellow solid. Selected data: 1H NMR (300 MHz, CDCl3) δ 9.51 (s, 1H), 7.53 (dd, J=5.92, 3.07 Hz, 1H), 7.46-7.36(m, 1H), 7.32 (dd, J=9.04, 4.60 Hz, 2H), 6.81 (d, J=2.29 Hz, 1H), 6.49 (d, J=2.28 Hz, 1H), 3.95 (s, J=7.48 Hz, 3H), 3.94-3.88(s, 3H), 2.51 (s, 3H); MS (APCI) m/z 297 [M+H]+.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. customThe layers were separated
  3. washthe organic layer was washed with water (2×50 mL), brine (50 mL)
  4. customdried
  5. concentrationconcentrated
  6. customThe crude solid was purified via CombiFlash

Sources & evidence

ORD record
ord-356f808ef7474067b07da0ae47d87f8d
Source dataset
uspto-grants-2011_11
Patent number
US08053440B2

Reaction notes

Loading…