o-Vanillin → HCID 67229763, compound

HRID 1367647Notes

Reaction equation

HRID 1367647 reaction equation
[CH3:1][C:2]1[N:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:10](=[O:18])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[OH:19][C:20]1[C:27]([O:28]C)=[CH:26][CH:25]=[CH:24][C:21]=1[CH:22]=O.[CH3:30]C([O-])=O.[Na+]>CC(O)=O>[OH:28][C:27]1[C:20]([O:19][CH3:30])=[C:21]([CH:22]=[CH:1][C:2]2[N:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:10](=[O:18])[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[N:3]=2)[CH:24]=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 8991o-VanillinHCID 633784(3H)-Quinazolinone, 2-methyl-3-phenyl-HCID 517045Sodium Acetate

Product 1

HCID 67229763HCID 67229763, compoundYield 75.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

In a 50 mL round-bottom flask a mixture of compound 27 (0.67 g, 0028 mol), 3-hydroxy-2-methoxy-benzaldehyde (9, 0.003 mol 0.45 g) and NaOAc (0.233 g, 0.002 mol) in AcOH was heated under reflux for 10 hours. After cooling the precipitate formed was filtered off, washed with water, dried and recrystallized from acetic acid to yield 28 (0.56 g, 55%). M. Wt. 370. LCMS [M+H]+=371.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 10 hours
  3. temperatureAfter cooling the precipitate
  4. customformed
  5. filtrationwas filtered off
  6. washwashed with water
  7. customdried
  8. customrecrystallized from acetic acid

Sources & evidence

ORD record
ord-1b0adfc23a144df98209d6b87fdfb4ae
Source dataset
uspto-grants-2011_02
Patent number
US07893260B2

Reaction notes

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