Hydrazine hydrate (1:1) → 1-(7-Amino-3,4-dihydroisoquinolin-2(1H)-yl)ethan-1-one

HRID 729234Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 729234
[C:1]([N:4]1[CH2:13][CH2:12][C:11]2[C:6](=[CH:7][C:8]([N+:14]([O-])=O)=[CH:9][CH:10]=2)[CH2:5]1)(=[O:3])[CH3:2].O.NN>CO>[C:1]([N:4]1[CH2:13][CH2:12][C:11]2[C:6](=[CH:7][C:8]([NH2:14])=[CH:9][CH:10]=2)[CH2:5]1)(=[O:3])[CH3:2]

Komponenten

4

Edukt 2

HCID 24654Hydrazine hydrate (1:1)HCID 64254731-(7-Nitro-3,4-dihydroisoquinolin-2(1H)-yl)ethanone

Produkt 1

HCID 128113521-(7-Amino-3,4-dihydroisoquinolin-2(1H)-yl)ethan-1-oneAusbeute 86,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of 13 (5.1 g, 23 mmol), activated carbon (4.2 g), ferric chloride hexahydrate (2.1 g, 7.6 mmol) and methanol (140 ml) is stirred under refluxing for 20 minutes. To the boiling mixture is added hydrazine hydrate (8.5 g, 265 mmol) dropwise, and the mixture is refluxed for an additional 4 h, cooled and filtered and the residue washed with methanol. The filtrate is concentrated in vacuo and the residue recrystallized from EtOAc to give compound 14 (3.8 g, 85% yield). 1H NMR [300 MHz, (CD3)2SO], a 3:2 mixture of amide conformers doubling most signals, δ 6.80 (1H, d, H-5), 6.40 (1H, d, H-6), 6.33 (1H, s, H-7), 4.89 (2H, br s, NH2), 4.46 (0.8H, s, ArCH2N), 4.41 (1.2H, s, ArCH2N), 3.57 (2H, t, ArCH2CH2N), 2.66 (1.2H, t, ArCH2CH2N), 2.55 (0.8H, t, ArCH2CH2N), 2.06 (1.2H, s, COCH3), 2.05 (1.8H, s COCH3).

Aufarbeitung

  1. temperatureunder refluxing for 20 minutes
  2. temperaturethe mixture is refluxed for an additional 4 h
  3. temperaturecooled
  4. filtrationfiltered
  5. washthe residue washed with methanol
  6. concentrationThe filtrate is concentrated in vacuo
  7. customthe residue recrystallized from EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-10052024dbfd4794a38efb33a52ab770
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07582616B2

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