1-Ethoxy-3,4-dihydroisoquinoline → HCID 178419894, compound

HRID 436445Notes

Reaction equation

HRID 436445 reaction equation
C(O[C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7][CH2:6][N:5]=1)C.[NH:14]([C:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:19][CH2:18][N:17]=1)[NH2:15]>CO>[N:15](=[C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7][CH2:6][NH:5]1)[N:14]=[C:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:19][CH2:18][NH:17]1

Participants

4

Reactant 2

HCID 123490381-Ethoxy-3,4-dihydroisoquinoline2×HCID 123490411-Hydrazinyl-3,4-dihydroisoquinoline

Product 1

HCID 178419894HCID 178419894, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of 1-ethoxy-3,4-dihydroisoquinoline (4.25 g.) and 1-hydrazino-3,4-dihydroisoquinoline (3.9 g.) in methanol (40 ml.) was stirred at room temperature overnight and then at reflux for a day. More 1-ethoxy-3,4-dihydroisoquinoline (1 g.) was added during the reflux period. The solution was stripped of methanol and the solid was recrystallized from 2-propanol, affording 1,1'-azinobis(1,2,3,4-tetrahydroisoquinoline) (II: Y=Y' =Z=Z' H) (first crop, 2.6 g., m.p. 178°-179° C.). In this example 1-hydrazino-3,4-dihydroisoquinoline hydrochloride can be used instead of 1-hydrazino-3,4-dihydroisoquinoline.

Workup

  1. temperatureat reflux for a day
  2. customthe solid was recrystallized from 2-propanol

Sources & evidence

ORD record
ord-0bfa69addef5474781e9dc01d85e0e9f
Source dataset
uspto-grants-1977_02
Patent number
US04009170

Reaction notes

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