o-Vanillin → HCID 5111379, compound

HRID 1038927Notes

Reaction equation

HRID 1038927 reaction equation
[CH3:1][C:2]1[N:11]([C:12]2[CH:13]=[C:14]([CH3:18])[CH:15]=[CH:16][CH:17]=2)[C:10](=[O:19])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[OH:20][C:21]1[C:28]([O:29][CH3:30])=[CH:27][CH:26]=[CH:25][C:22]=1[CH:23]=O.CC([O-])=O.[Na+]>CC(O)=O>[OH:20][C:21]1[C:28]([O:29][CH3:30])=[CH:27][CH:26]=[CH:25][C:22]=1[CH:23]=[CH:1][C:2]1[N:11]([C:12]2[CH:13]=[C:14]([CH3:18])[CH:15]=[CH:16][CH:17]=2)[C:10](=[O:19])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

5

Reactant 3

HCID 8991o-VanillinHCID 631354(3H)-Quinazolinone, 2-methyl-3-(m-tolyl)-HCID 517045Sodium Acetate

Product 1

HCID 5111379HCID 5111379, compoundYield 96.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

In a 50 mL round-bottom flask a mixture of 50 (0.5 g, 002 mol), 2-hydroxy-3 methoxybenzaldehyde (0.4 g, 0.0025 mol) 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 51 (0.74 g, 85%). M. Wt. 384. LCMS [M+H]+=385.

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-e37309df76f74f55a94c62272c8bcb5c
Source dataset
uspto-grants-2013_10
Patent number
US08552009B2

Reaction notes

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