Hydrochloric Acid → 1-Benzyl-2-methyl-1,4,5,6-tetrahydro-1,3,6-triaza-benzo[e]azulene

HRID 220784Notes

Reaction equation

HRID 220784 reaction equation
[CH2:1]([N:8]1[C:17]2[C:16]3[CH:18]=[CH:19][CH:20]=[CH:21][C:15]=3[N:14](C(C3C=CC=CC=3)=O)[CH2:13][CH2:12][C:11]=2[N:10]=[C:9]1[CH3:30])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>CO>[CH2:1]([N:8]1[C:17]2[C:16]3[CH:18]=[CH:19][CH:20]=[CH:21][C:15]=3[NH:14][CH2:13][CH2:12][C:11]=2[N:10]=[C:9]1[CH3:30])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57555380(1-Benzyl-2-methyl-4,5-dihydro-1H-1,3,6-triaza-benzo[e]azulen-6-yl)-phenyl-methanone

Product 1

HCID 575554001-Benzyl-2-methyl-1,4,5,6-tetrahydro-1,3,6-triaza-benzo[e]azuleneYield 78%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(1-Benzyl-2-methyl-4,5-dihydro-1H-1,3,6-triaza-benzo[e]azulen-6-yl)-phenyl-methanone from Example E5a.1 (5.73 g, 14.6 mmol) was placed in methanol (50 ml) and a 6M HCl aqueous solution (200 ml) was added. The reaction mixture was heated at reflux for 18 h then concentrated in vacuo. The residue was dissolved in dichloromethane, basified with saturated NaHCO3 then washed with brine, dried and concentrated in vacuo to yield the title compound (3.30 g, 78%).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 18 h
  3. concentrationthen concentrated in vacuo
  4. dissolutionThe residue was dissolved in dichloromethane
  5. washthen washed with brine
  6. customdried
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8d1cb204aea94ec686d6fbc7019208dc
Source dataset
uspto-grants-2012_06
Patent number
US08202858B2

Reaction notes

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