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

HRID 436432

Reaktionsgleichung

Reaktionsgleichung von HRID 436432
[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]

Komponenten

6

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

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.).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-094a02f11dc94b20987158205f53cf8c
Quelldatensatz
uspto-grants-1977_02
Patentnummer
US04009170

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