Salicylaldehyde → 15666-67-8

HRID 1576374Notes

Reaction equation

HRID 1576374 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[NH2:12])[CH:5]=[CH:4][CH:3]=1.[CH:13](=O)[C:14]1[C:15](=[CH:17][CH:18]=[CH:19][CH:20]=1)[OH:16]>C(O)C.[Pd]>[OH:16][C:15]1[CH:17]=[CH:18][CH:19]=[CH:20][C:14]=1[C:13]1[NH:1][C:2]2[CH:3]=[CH:4][CH:5]=[C:6]3[C:11]=2[C:10]([N:12]=1)=[CH:9][CH:8]=[CH:7]3

Participants

5

Reactant 2

HCID 6998SalicylaldehydeHCID 680671,8-Diaminonaphthalene

Product 1

HCID 13559665015666-67-8

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To 1,8-diaminonaphthalene (31.6 g, 0.2 mole) suspended in 200 ml absolute ethanol is added salicylaldehyde (24.4 g, 0.2 mole) and 7 g 10% palladium-on-carbon. The mixture is stirred and heated under reflux for 45 min., after which it is allowed to stand for 18 hours at ambient temperature. The mixture is then filtered and the filtrate is washed with ethanol and ether. The green solid is treated with heated dimethylformamide (charcoal) and filtered hot. The catalyst is removed from the product by filtration along with the charcoal. The yellow-orange filtrate is cooled, and upon addition of water, yields the desired product, 2-(o-hydroxyphenyl)perimidine, orange crystals, m.p. 258°-260° dec.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 45 min.
  3. filtrationThe mixture is then filtered
  4. washthe filtrate is washed with ethanol and ether
  5. additionThe green solid is treated with heated dimethylformamide (charcoal)
  6. filtrationfiltered hot
  7. customThe catalyst is removed from the product by filtration along with the charcoal
  8. temperatureThe yellow-orange filtrate is cooled
  9. additionupon addition of water

Sources & evidence

ORD record
ord-df9ece264b46479897f4022fe61db98f
Source dataset
uspto-grants-1976_09
Patent number
US03980782

Reaction notes

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