Methylamine → HCID 21493546, compound

HRID 1973255Notes

Reaction equation

HRID 1973255 reaction equation
Br[CH2:2][C:3]1[C:4]2[C:9]([C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=3[C:16]=1[CH2:17]Br)=[CH:8][CH:7]=[CH:6][CH:5]=2.[CH3:19][NH2:20]>CO>[CH3:19][N:20]1[CH2:17][C:16]2[C:3](=[C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:9]3=[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:15]3=2)[CH2:2]1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 4663482Phenanthrene, 9,10-bis(bromomethyl)-

Product 1

HCID 21493546HCID 21493546, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

13.4 g of 9,10-bis-bromomethyl-phenanthrene [see S. Hauptmann, Chem. Ber. 93, 2604 (1960)] is added within one hour, with stirring, to a solution of 37.5 g of methylamine in 225 ml of methanol, with the reaction temperature being maintained at 45°-50°. The reaction mixture is stirred for a further hour at 50°, and the solvent and excess methylamine are subsequently distilled off. 50 ml of water is added to the residue, and the formed suspension is extracted with ether. The ethereal solution is washed with water, dried over potassium carbonate and concentrated by evaporation. The residue is recrystallised from acetone to yield 2-methyl-2,3-dihydro-1H-dibenz[e,g]isoindole, m.p. 122°-123°.

Workup

  1. temperaturebeing maintained at 45°-50°
  2. distillationthe solvent and excess methylamine are subsequently distilled off
  3. addition50 ml of water is added to the residue
  4. extractionthe formed suspension is extracted with ether
  5. washThe ethereal solution is washed with water
  6. dry with materialdried over potassium carbonate
  7. concentrationconcentrated by evaporation
  8. customThe residue is recrystallised from acetone

Sources & evidence

ORD record
ord-261de9e471a142768f627eaf94d41fa4
Source dataset
uspto-grants-1976_12
Patent number
US03996373

Reaction notes

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