Benzaldehyde → 1-(2-Benzylidenehydrazino)-3,4-dihydroisoquinoline

HRID 436435Notes

Reaction equation

HRID 436435 reaction equation
[NH:1]([C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][CH2:5][N:4]=1)[NH2:2].[CH:13](=O)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.Cl>>[CH:13](=[N:2][NH:1][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][CH2:5][N:4]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 3

HCID 240BenzaldehydeHCID 313Hydrochloric AcidHCID 123490411-Hydrazinyl-3,4-dihydroisoquinoline

Product 1

HCID 571050551-(2-Benzylidenehydrazino)-3,4-dihydroisoquinoline

Procedure

In a manner similar to that of Example 4, condensation of 1-hydrazino-3,4-dihydroisoquinoline (7 g.) and benzaldehyde (5.5 g.) and treatment of the reaction mixture with hydrochloric acid gave a solid, which was recrystallized from ethanol-ether, affording 1-(2-benzylidenehydrazino)-3,4-dihydroisoquinoline (I: X=C6H5, X'=Y=Y'=Z=Z'=H) hydrochloride (11.6 g., m.p. 226°-228° C.).

Workup

  1. customgave a solid, which
  2. customwas recrystallized from ethanol-ether

Sources & evidence

ORD record
ord-609a5292a0ef4029a99879ba7f968f0f
Source dataset
uspto-grants-1977_02
Patent number
US04009170

Reaction notes

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