Acetic Acid → HCID 86754439, compound

HRID 617233Notes

Reaction equation

HRID 617233 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.[CH:18](=O)[C:19]1[C:20](=[CH:22][CH:23]=[CH:24][CH:25]=1)[OH:21].[BH4-].[Na+].[C:29]([OH:32])(=[O:31])[CH3:30]>C(O)C>[C:29]([OH:32])(=[O:31])[CH3:30].[C:29]([OH:32])(=[O:31])[CH3:30].[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:12][CH2:13][C:14]([CH3:17])([NH:16][CH2:18][C:19]3[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=3[OH:21])[CH3:15])=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6998SalicylaldehydeHCID 4311764Sodium borohydrideHCID 54478391HCID 54478391, compound

Product 1

HCID 86754439HCID 86754439, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.25 g of N1 -(7-chloro-quinolin-4-yl)-2-methyl-propane-1,2-diamine and 0.54 g of salicylaldehyde were stirred under reflux overnight in the presence of 1.25 g of molecular sieve (E. Merck, 3 Å). Thereafter, the mixture was filtered and the solvent was evaporated. From a small amount of diethyl ether and ethyl acetate there was obtained a crystalline product which was again taken up in 20 ml of ethanol. After the addition of 0.19 g of sodium borohydride the mixture was left to react overnight, thereafter 5 ml of glacial acetic acid were added thereto and the mixture was evaporated to dryness. After the addition of 10 ml of methanol the mixture was again evaporated. Addition of methanol and evaporation were repeated twice. The residue was then crystallized from 10 ml of ethanol. 0.9 g (40%) of colourless crystalline product of m.p. 150° C. was obtained.

Workup

  1. temperatureunder reflux overnight in the presence of 1.25 g of molecular sieve (E. Merck, 3 Å)
  2. filtrationThereafter, the mixture was filtered
  3. customthe solvent was evaporated
  4. customFrom a small amount of diethyl ether and ethyl acetate there was obtained a crystalline product which
  5. waitwas left
  6. customto react overnight
  7. customthe mixture was evaporated to dryness
  8. additionAfter the addition of 10 ml of methanol the mixture
  9. customwas again evaporated
  10. additionAddition of methanol and evaporation
  11. customThe residue was then crystallized from 10 ml of ethanol

Sources & evidence

ORD record
ord-cdad9a9e2ff6473c9539379d9e63c718
Source dataset
uspto-grants-1999_09
Patent number
US05948791

Reaction notes

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