Formaldehyde → 9-(N-benzyl-N-butylaminomethyl)-6-methyl-1,2,3,4,7,8,9,10-octahydro-benzo[f]quinoline-3,10-dione

HRID 1719860Notes

Reaction equation

HRID 1719860 reaction equation
Cl.[CH2:2]([NH:9][CH2:10][CH2:11][CH2:12][CH3:13])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH2:14]=O.[CH3:16][C:17]1[C:18]2[CH2:31][CH2:30][CH2:29][C:28](=[O:32])[C:19]=2[C:20]2[CH2:21][CH2:22][C:23](=[O:27])[NH:24][C:25]=2[CH:26]=1>C(OC(=O)C)(=O)C>[CH2:2]([N:9]([CH2:14][CH:29]1[C:28](=[O:32])[C:19]2[C:20]3[CH2:21][CH2:22][C:23](=[O:27])[NH:24][C:25]=3[CH:26]=[C:17]([CH3:16])[C:18]=2[CH2:31][CH2:30]1)[CH2:10][CH2:11][CH2:12][CH3:13])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 176997N-benzylbutan-1-amine HydrochlorideHCID 130517676-Methyl-1,2,3,4,7,8,9,10-octahydro-benzo[f]quinoline-3,10-dione

Product 1

HCID 133244479-(N-benzyl-N-butylaminomethyl)-6-methyl-1,2,3,4,7,8,9,10-octahydro-benzo[f]quinoline-3,10-dione

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

N-Benzyl-N-butylamine hydrochloride (12 g), 6 ml of 37% formalin, 40 ml of acetic anhydride and 11.5 g of 6-methyl-1,2,3,4,7,8,9,10-octahydro-benzo[f]quinoline-3,10-dione are allowed to react and post-treated in the same manner of Example 1. The obtained crystals are recrystallized from isopropanol to give 13.2 g of 9-(N-benzyl-N-butylaminomethyl)-6-methyl-1,2,3,4,7,8,9,10-octahydro-benzo[f]quinoline-3,10-dione as colorless needles, melting at 190°-193° C.

Workup

  1. customto react
  2. additionpost-treated in the same manner of Example 1
  3. customThe obtained crystals are recrystallized from isopropanol

Sources & evidence

ORD record
ord-b0eebc3e299b4f27b8175d8ab3270e60
Source dataset
uspto-grants-1985_09
Patent number
US04543354

Reaction notes

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