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

HRID 1719862Notes

Reaction equation

HRID 1719862 reaction equation
[ClH:1].[CH2:2]([NH2:10])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH2:11]=O.[CH3:13][C:14]1[C:15]2[CH2:28][CH2:27][CH2:26][C:25](=[O:29])[C:16]=2[C:17]2[CH2:18][CH2:19][C:20](=[O:24])[NH:21][C:22]=2[CH:23]=1>C(O)C>[ClH:1].[CH3:13][C:14]1[C:15]2[CH2:28][CH2:27][CH:26]([CH2:11][NH:10][CH2:2][CH2:3][C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=3)[C:25](=[O:29])[C:16]=2[C:17]2[CH2:18][CH2:19][C:20](=[O:24])[NH:21][C:22]=2[CH:23]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 90752-Phenylethylamine hydrochlorideHCID 130517676-Methyl-1,2,3,4,7,8,9,10-octahydro-benzo[f]quinoline-3,10-dione

Product 1

HCID 202659946-Methyl-1,2,3,4,7,8,9,10-octahydro-9-phenethylaminomethylbenzo[f]quinoline-3,10-dione hydrochlorideYield 25%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Phenethylamine hydrochloride (4.7 g), 2.7 g of paraformaldehyde and 4.6 g of 6-methyl-1,2,3,4,7,8,9,10-octahydro-benzo[f]quinoline-3,10-dione are added to 200 ml of ethanol, and the mixture is stirred under reflux for 2 days. The reaction mixture is then cooled, and the precipitated crystals are collected by filtration and recrystallized from 60% ethanol to give 2.0 g of 6-methyl-1,2,3,4,7,8,9,10-octahydro-9-phenethylaminomethylbenzo[f]quinoline-3,10-dione hydrochloride as colorless needles, melting at 190°-192° C.

Workup

  1. temperatureunder reflux for 2 days
  2. temperatureThe reaction mixture is then cooled
  3. filtrationthe precipitated crystals are collected by filtration
  4. customrecrystallized from 60% ethanol

Sources & evidence

ORD record
ord-eb14c08b328f47a29b57faac380b3442
Source dataset
uspto-grants-1985_09
Patent number
US04543354

Reaction notes

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