Acetaldehyde → 1-(2-Ethylidenehydrazino)-3,4-dihydroisoquinoline

HRID 436432

Reaction equation

HRID 436432 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)[CH3:14].C(O)C.S(=O)(=O)(O)O>CCOCC>[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)[CH3:14]

Participants

6

Reactant 4

HCID 177AcetaldehydeHCID 702EthanolHCID 1118Sulfuric AcidHCID 123490411-Hydrazinyl-3,4-dihydroisoquinoline

Product 1

HCID 572691501-(2-Ethylidenehydrazino)-3,4-dihydroisoquinoline

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

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. customto stand at room temperature
  2. custom(for 45 min)
  3. customThe resulting oil crystallized
  4. customthe crystals were recrystallized from ethanol-ether

Sources & evidence

ORD record
ord-094a02f11dc94b20987158205f53cf8c
Source dataset
uspto-grants-1977_02
Patent number
US04009170

Linked notes

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