Acetic Anhydride → Pyrrolo(4,3,2-de)(1,2,4)triazolo(3,4-a)isoquinoline, 4,6-dihydro-8-methyl-

HRID 1284036Notes

Reaction equation

HRID 1284036 reaction equation
Cl.[NH:2]([C:4]1[C:13]2[CH:12]=[CH:11][CH:10]=[C:9]3[NH:14][CH:15]=[C:7]([C:8]=23)[CH2:6][N:5]=1)[NH2:3].[C:16](OC(=O)C)(=O)[CH3:17].C(=O)(O)[O-].[Na+]>>[CH3:16][C:17]1[N:5]2[CH2:6][C:7]3[C:8]4[C:9]([NH:14][CH:15]=3)=[CH:10][CH:11]=[CH:12][C:13]=4[C:4]2=[N:2][N:3]=1

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 3041086Pyrrolo(4,3,2-de)isoquinolin-5(1H)-one, 3,4-dihydro-, hydrazone, monohydrochloride

Product 1

HCID 3041158Pyrrolo(4,3,2-de)(1,2,4)triazolo(3,4-a)isoquinoline, 4,6-dihydro-8-methyl-

Procedure

5-Hydrazino-1,3-dihydropyrrolo[4,3,2-de]isoquinoline hydrochloride (50 mg), described in Example 8, is heated at reflux with 3 ml of acetic anhydride for 2 hours. The mixture is cooled and then poured into a saturated solution of sodium bicarbonate. The resulting precipitate is collected and then dissolved in methanol. This solution is rendered acidic by the addition of HCl in ether. The mixture is treated with charcoal and concentrated to give the title compound.

Workup

  1. temperatureis heated
  2. temperatureThe mixture is cooled
  3. customThe resulting precipitate is collected
  4. dissolutiondissolved in methanol
  5. additionThis solution is rendered acidic by the addition of HCl in ether
  6. additionThe mixture is treated with charcoal
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-a7bb1d60d56f46199cfb1b62a51a5100
Source dataset
uspto-grants-1976_08
Patent number
US03978066

Reaction notes

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