Formaldehyde → 9-Diethylaminomethyl-6-methyl-1,2,3,4,7,8,9,10-octahydro-benzo[f]quinoline-3,10-dione hydrochloride

HRID 1719859Notes

Reaction equation

HRID 1719859 reaction equation
[ClH:1].[CH2:2]([NH:4][CH2:5][CH3:6])[CH3:3].[CH2:7]=O.[CH3:9][C:10]1[C:11]2[CH2:24][CH2:23][CH2:22][C:21](=[O:25])[C:12]=2[C:13]2[CH2:14][CH2:15][C:16](=[O:20])[NH:17][C:18]=2[CH:19]=1>C(OC(=O)C)(=O)C>[ClH:1].[CH2:2]([N:4]([CH2:7][CH:22]1[C:21](=[O:25])[C:12]2[C:13]3[CH2:14][CH2:15][C:16](=[O:20])[NH:17][C:18]=3[CH:19]=[C:10]([CH3:9])[C:11]=2[CH2:24][CH2:23]1)[CH2:5][CH3:6])[CH3:3]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 10197650Diethylammonium chlorideHCID 130517676-Methyl-1,2,3,4,7,8,9,10-octahydro-benzo[f]quinoline-3,10-dione

Product 1

HCID 202660539-Diethylaminomethyl-6-methyl-1,2,3,4,7,8,9,10-octahydro-benzo[f]quinoline-3,10-dione hydrochloride

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

Diethylamine hydrochloride (8.3 g) is mixed with 6 ml of 37% formalin at room temperature for 30 minutes whereupon 40 ml of acetic anhydride is added dropwise at 60°-70° C. with stirring. After about 1 hour 11.5 g of 6-methyl-1,2,3,4,7,8,9,10-octahydro-benzo[f]quinoline-3,10-dione is added, and the resulting mixture is kept at 60°-70° C. for 3 hours. The reaction mixture is then concentrated under reduced pressure. To the residue is added 200 ml of acetone, and the mixture is heated under reflux for 10 minutes and then allowed to stand at room temperature. The precipitated crystals are collected by filtration and recrystallized from ethanol to give 7.0 g of 9-diethylaminomethyl-6-methyl-1,2,3,4,7,8,9,10-octahydro-benzo[f]quinoline-3,10-dione hydrochloride as colorless needles, melting at 196°-197° C.

Workup

  1. additionis added dropwise at 60°-70° C.
  2. concentrationThe reaction mixture is then concentrated under reduced pressure
  3. additionTo the residue is added 200 ml of acetone
  4. temperaturethe mixture is heated
  5. temperatureunder reflux for 10 minutes
  6. customto stand at room temperature
  7. filtrationThe precipitated crystals are collected by filtration
  8. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-1832a03952ed41da9b9e82ffc0b26ac8
Source dataset
uspto-grants-1985_09
Patent number
US04543354

Reaction notes

Loading…