3,4-Dichlorobenzaldehyde → HCID 70201850, compound

HRID 617231Notes

Reaction equation

HRID 617231 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.[Cl:18][C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][C:26]=1[Cl:27])[CH:22]=O>C(O)C>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:12][CH2:13][C:14]([CH3:17])([NH:16][CH2:22][C:21]3[CH:24]=[CH:25][C:26]([Cl:27])=[C:19]([Cl:18])[CH:20]=3)[CH3:15])=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 227103,4-DichlorobenzaldehydeHCID 54478391HCID 54478391, compound

Product 1

HCID 70201850HCID 70201850, 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 0.88 g of 3,4-dichlorobenzaldehyde were heated under reflux in 10 ml of ethanol for 3 hours. In order to complete the reaction, the solvent was evaporated in a vacuum. The resulting Schiff's base was again taken up in 20 ml of ethanol and reduced to the amine by the addition of 0.19 g of sodium borohydride. Excess reducing agent was decomposed after 2 hours by the addition of 10 ml of glacial acetic acid. The turbid solution was then evaporated on a rotary evaporator. 10 ml of methanol were added to the residue and the mixture was again evaporated. Addition of methanol and evaporation were repeated twice. The evaporation residue was then taken up in 25 ml of water. The pH was adjusted to 10 by the addition of dilute sodium hydroxide solution, separating the product. The product was purified by recrystallization from 45 ml of ethyl acetate. Yield: 1.09 g (53%), m.p. 178-179° C.

Workup

  1. customthe reaction
  2. customthe solvent was evaporated in a vacuum
  3. additionreduced to the amine by the addition of 0.19 g of sodium borohydride
  4. additionwas decomposed after 2 hours by the addition of 10 ml of glacial acetic acid
  5. customThe turbid solution was then evaporated on a rotary evaporator
  6. addition10 ml of methanol were added to the residue
  7. customthe mixture was again evaporated
  8. additionAddition of methanol and evaporation
  9. additionThe pH was adjusted to 10 by the addition of dilute sodium hydroxide solution
  10. customseparating the product
  11. customThe product was purified by recrystallization from 45 ml of ethyl acetate

Sources & evidence

ORD record
ord-ef65824bd7724a9589b5dac16fc270f9
Source dataset
uspto-grants-1999_09
Patent number
US05948791

Reaction notes

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