Acetone → Pyrrolo(4,3,2-de)isoquinolin-5(1H)-one, 3,4-dihydro-, (1-methylethylidene)hydrazone

HRID 1284034Notes

Reaction equation

HRID 1284034 reaction equation
[NH:1]([C:3]1[C:12]2[CH:11]=[CH:10][CH:9]=[C:8]3[NH:13][CH:14]=[C:6]([C:7]=23)[CH2:5][N:4]=1)[NH2:2].C.[CH3:16][C:17]([CH3:19])=O>>[C:17](=[N:2][NH:1][C:3]1[C:12]2[CH:11]=[CH:10][CH:9]=[C:8]3[NH:13][CH:14]=[C:6]([C:7]=23)[CH2:5][N:4]=1)([CH3:19])[CH3:16]

Participants

4

Reactant 3

HCID 180AcetoneHCID 297MethaneHCID 30410875-Hydrazino-1,3-dihydropyrrolo[4,3,2-de]isoquinoline

Product 1

HCID 3044458Pyrrolo(4,3,2-de)isoquinolin-5(1H)-one, 3,4-dihydro-, (1-methylethylidene)hydrazone

Procedure

5-Hydrazino-1,3-dihydropyrrolo[4,3,2-de]isoquinoline (4.5 g), described in Example 8, is boiled in acetone (ca. 50 ml) for 10 minutes. The reaction mixture is treated with charcoal, filtered and concentrated. Addition of ether-hexane gives a precipitate. The precipitate is recrystallized from benzenemethanol-ether to give the title compound, mp 200° - 201°C, νmaxnujol 3450, 3100, 1625, 1565, 1540 and 1510 cm-1.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated
  3. additionAddition of ether-hexane
  4. customgives a precipitate
  5. customThe precipitate is recrystallized from benzenemethanol-ether

Sources & evidence

ORD record
ord-67103b627a5a491095c6b7c8c456d654
Source dataset
uspto-grants-1976_08
Patent number
US03978066

Reaction notes

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