Hydrochloric Acid → 1-[2-(3,5-Dimethoxy-4-hydroxybenzylidene)hydrazino]-3,4-dihydroisoquinoline

HRID 436437Notes

Reaction equation

HRID 436437 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:24]=[C:21]([O:22][CH3:23])[C:19]([OH:20])=[C:16]([O:17][CH3:18])[CH:15]=1.Cl>>[CH3:23][O:22][C:21]1[CH:24]=[C:14]([CH:15]=[C:16]([O:17][CH3:18])[C:19]=1[OH:20])[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

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 8655SyringaldehydeHCID 123490411-Hydrazinyl-3,4-dihydroisoquinoline

Product 1

HCID 1360023911-[2-(3,5-Dimethoxy-4-hydroxybenzylidene)hydrazino]-3,4-dihydroisoquinoline

Procedure

In a manner similar to that of Example 4, condensation of 1-hydrazino-3,4-dihydroisoquinoline (10.0 g.) and syringaldehyde (12.5 g.) and treatment of the reaction mixture with hydrochloric acid gave a solid, which was recrystallized from N,N-dimethylformamide-ether, affording 1-[2-(3,5-dimethoxy-4-hydroxybenzylidene)hydrazino]-3,4-dihydroisoquinoline (I: X=3,5-(CH3O)2 -4-HOC6H2, X'=Y=Y'=Z=Z'=H) hydrochloride in two crops (total of 18 g., m.p. 232°-233° C.).

Workup

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

Sources & evidence

ORD record
ord-fcc0816ca09341248f9561780acf4a5e
Source dataset
uspto-grants-1977_02
Patent number
US04009170

Reaction notes

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