o-Vanillin → HCID 136400709, compound

HRID 1038929Notes

Reaction equation

HRID 1038929 reaction equation
[CH3:1][C:2]1[N:11]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([Cl:19])[CH:13]=2)[C:10](=[O:20])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[OH:21][C:22]1[C:29]([O:30][CH3:31])=[CH:28][CH:27]=[CH:26][C:23]=1[CH:24]=O.CC([O-])=O.[Na+]>CC(O)=O>[Cl:19][C:14]1[CH:13]=[C:12]([N:11]2[C:10](=[O:20])[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[N:3]=[C:2]2[CH:1]=[CH:24][C:23]2[CH:26]=[CH:27][CH:28]=[C:29]([O:30][CH3:31])[C:22]=2[OH:21])[CH:17]=[CH:16][C:15]=1[Cl:18]

Participants

5

Reactant 3

HCID 8991o-VanillinHCID 517045Sodium AcetateHCID 5888673-(3,4-dichlorophenyl)-2-methylquinazolin-4-one

Product 1

HCID 136400709HCID 136400709, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Compound 63 (1 g, 0.028 mol), 2-hydroxy-3 methoxybenzaldehyde (9, 0.4 g, 0.003 mol) and NaOAc (0.233 g, 0.002 mol) in AcOH were heated under reflux for 10 hours. After cooling the precipitate formed was washed with water, filtered off, dried and recrystallized from EtOH to yield 64 (0.55 g, 71%). M. Wt. 439. LCMS [M+H]+=440.

Workup

  1. temperatureunder reflux for 10 hours
  2. temperatureAfter cooling the precipitate
  3. customformed
  4. washwas washed with water
  5. filtrationfiltered off
  6. customdried
  7. customrecrystallized from EtOH

Sources & evidence

ORD record
ord-a65d247d12a14c8399024d94c6cc28f4
Source dataset
uspto-grants-2013_10
Patent number
US08552009B2

Reaction notes

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