Hydrazinium chloride → 1-Hydrazino-3,4-dihydroisoquinoline hydrochloride

HRID 436431Notes

Reaction equation

HRID 436431 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.[ClH:14].[NH2:15][NH2:16]>C(O)C>[ClH:14].[NH:15]([C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7][CH2:6][N:5]=1)[NH2:16]

Participants

4

Reactant 2

HCID 115031Hydrazinium chlorideHCID 123490381-Ethoxy-3,4-dihydroisoquinoline

Product 1

HCID 214525621-Hydrazino-3,4-dihydroisoquinoline hydrochlorideYield 79.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1-ethoxy-3,4-dihydroisoquinoline (1.0 g.), hydrazine monohydrochloride (0.4 g.) and absolute ethanol (15 ml.) was heated under reflux (for 40 min.). The solution was cooled, filtered and concentrated and the residue was recrystallized from ethanol-ether, affording 1-hydrazino-3,4-dihydroisoquinoline hydrochloride (0.9 g., m.p. 205°-207° C.). C. A mixture of 1-hydrazino-3,4-dihydroisoquinoline (8.0 g.), acetaldehyde (20 ml.) and ethanol (20 ml.) was allowed to stand at room temperature (for 45 min). Ethanolic sulfuric acid was added until the solution was distinctly acidic. Ether was added. The resulting oil crystallized and the crystals were recrystallized from ethanol-ether, affording 1-(2-ethylidenehydrazino)-3,4-dihydroisoquinoline (I: X=CH3, X'=Y=Y'=Z=Z'=H) sulfate in two crops (8.3 g., m.p. 152°-154° C.; 0.5 g., m.p. 152°-155° C.).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux (for 40 min.)
  3. temperatureThe solution was cooled
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customthe residue was recrystallized from ethanol-ether

Sources & evidence

ORD record
ord-2fe5d4827699491496fd61f7c51c25e5
Source dataset
uspto-grants-1977_02
Patent number
US04009170

Reaction notes

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