3-Isopropoxy-4-methoxybenzaldehyde → HCID 9863181, compound

HRID 1067381Notes

Reaction equation

HRID 1067381 reaction equation
[CH:1]([O:4][C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][C:12]=1[O:13][CH3:14])[CH:8]=O)([CH3:3])[CH3:2].[N:15]1([C:20]2[CH:25]=[CH:24][C:23]([NH2:26])=[C:22]([NH2:27])[CH:21]=2)[CH:19]=[N:18][CH:17]=[N:16]1>CO>[CH:1]([O:4][C:5]1[CH:6]=[C:7]([C:8]2[NH:27][C:22]3[CH:21]=[C:20]([N:15]4[CH:19]=[N:18][CH:17]=[N:16]4)[CH:25]=[CH:24][C:23]=3[N:26]=2)[CH:10]=[CH:11][C:12]=1[O:13][CH3:14])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 5920923-Isopropoxy-4-methoxybenzaldehydeHCID 10397291HCID 10397291, compound

Product 1

HCID 9863181HCID 9863181, compoundYield 70.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Under reflux, 20 ml of methanol solution containing 4.27 g of 3-isopropoxy-4 -methoxybenzaldehyde and 10.81 g of ferric chloride hexahydrate was added dropwise to 35 ml of methanol solution containing 3.50 g of 4-(1,2,4-triazol-1-yl)-o-phenylenediamine obtained in Reference Example 2. The resulting mixture was refluxed for 1 hour and then cooled, and the insoluble matter was collected by filtration. This was suspended in ethyl acetate/water and alkalified with liquid ammonia, and then the insoluble matter was removed by Celite filtration. The ethyl acetate layer was collected and dried over magnesium sulfate, and then the solvent was evaporated. By crystallizing the resulting residue with ethyl acetate/hexane, 4.92 g (70%) of the title compound was obtained. Its physical property values coincided with the data obtained in the above step (1).

Workup

  1. temperatureUnder reflux
  2. customobtained in Reference Example 2
  3. temperatureThe resulting mixture was refluxed for 1 hour
  4. temperaturecooled
  5. filtrationthe insoluble matter was collected by filtration
  6. customthe insoluble matter was removed by Celite filtration
  7. customThe ethyl acetate layer was collected
  8. dry with materialdried over magnesium sulfate
  9. customthe solvent was evaporated
  10. customBy crystallizing the resulting residue with ethyl acetate/hexane

Sources & evidence

ORD record
ord-c01f2d9b57674b4e9711c051bd5eccdb
Source dataset
uspto-grants-2001_06
Patent number
US06248768B1

Reaction notes

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