2-Hydroxy-4-Methoxybenzaldehyde → HCID 70199588, compound

HRID 617234Notes

Reaction equation

HRID 617234 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:12][CH2:13][C:14]([CH3:17])([NH2:16])[CH3:15])=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.[OH:18][C:19]1[CH:26]=[C:25]([O:27][CH3:28])[CH:24]=[CH:23][C:20]=1[CH:21]=O>C(O)C>[ClH:1].[ClH:1].[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:12][CH2:13][C:14]([CH3:17])([NH:16][CH2:21][C:20]3[CH:23]=[CH:24][C:25]([O:27][CH3:28])=[CH:26][C:19]=3[OH:18])[CH3:15])=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 696002-Hydroxy-4-MethoxybenzaldehydeHCID 54478391HCID 54478391, compound

Product 1

HCID 70199588HCID 70199588, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.25 g of N1 -(7-chloro-quinolin-4-yl)-2-methyl-propane-1,2-diamine and 0.76 g of 2-hydroxy-4-methoxy-benzaldehyde were stirred under reflux overnight in 20 ml of ethanol in the presence of 1.25 g of molecular sieve (E. Merck, 3 Å). The mixture was filtered, the solvent was evaporated and the residue was again taken up in 20 ml of ethanol. After the addition of 0.19 g of sodium borohydride the mixture was stirred at room temperature for 6 hours, thereafter 5 ml of glacial acetic acid were added thereto and the mixture was evaporated to dryness. 10 ml of methanol were added to the residue and the mixture was again evaporated. Addition of methanol and evaporation were repeated twice. Finally, the residue was taken up in 10 ml of hot ethanol, 10 ml of 3N isopropanolic hydrochloric acid were added thereto and the product was left to crystallize out as the dihydrochloride. Yield 1.8 g (78%) of colourless crystalline powder, m.p. 220° C.

Workup

  1. filtrationThe mixture was filtered
  2. customthe solvent was evaporated
  3. additionAfter the addition of 0.19 g of sodium borohydride the mixture
  4. addition5 ml of glacial acetic acid were added
  5. customthe mixture was evaporated to dryness
  6. addition10 ml of methanol were added to the residue
  7. customthe mixture was again evaporated
  8. additionAddition of methanol and evaporation
  9. addition10 ml of 3N isopropanolic hydrochloric acid were added
  10. waitthe product was left
  11. customto crystallize out as the dihydrochloride

Sources & evidence

ORD record
ord-823e6994f111411ab917055b5d7fe18c
Source dataset
uspto-grants-1999_09
Patent number
US05948791

Reaction notes

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