Ethyl formate → 3-Amino-2,3-dihydro-1H-inden-5-ol

HRID 380628Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 380628
C[O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][CH2:8][CH:9]2[NH:12][CH3:13])=[CH:5][CH:4]=1.C[O:15][C:16]1[CH:24]=[C:23]2[C:19]([CH2:20][CH2:21][CH:22]2[NH2:25])=[CH:18][CH:17]=1.C(O[CH2:29][CH3:30])=O.[H-].[H-].[H-].[H-].[Li+].[Al+3]>>[CH3:13][NH:12][CH:9]1[C:10]2[C:6](=[CH:5][CH:4]=[C:3]([OH:2])[CH:11]=2)[CH2:7][CH2:8]1.[CH2:29]([NH:25][CH:22]1[C:23]2[C:19](=[CH:18][CH:17]=[C:16]([OH:15])[CH:24]=2)[CH2:20][CH2:21]1)[CH3:30].[OH:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][CH2:8][CH:9]2[NH2:12])=[CH:5][CH:4]=1

Komponenten

7

Edukt 4

HCID 8025Ethyl formateHCID 99204636-Methoxy-1-IndanamineHCID 18619882HCID 18619882, VerbindungHCID 21226445Aluminium lithium hydride

Produkt 3

HCID 148734623-Amino-2,3-dihydro-1H-inden-5-olHCID 18619880HCID 18619880, VerbindungHCID 18619885HCID 18619885, Verbindung

Versuchsvorschrift

N-Methyl-6-hydroxy-1-aminoindan was prepared by demethylation of 6-methoxy-N-methyl-1-aminoindan, which was prepared from 6-methoxy-1-aminoindan by reductive alkylation (e.g. ethyl formate, followed by LiAlH4 reduction), or alternatively, by reductive amination (MeNH2, HCl, NaCNBH3) of 6-methoxy-1-indanone2. N-ethyl-6-hydroxy-1-aminoindan was obtained by acetylation of 6-hydroxy-1-aminoindan (Ac2O, KOH), followed by reduction (LiAlH4). N,N-Dimethyl-6-hydroxy-1-aminoindan was prepared by demethylation of the corresponding 6-methoxy analogue, which was prepared by reduction alkylation (formaldehyde, formic acid) of 6-methoxy-1-aminoindan. 4-Hydroxy-1-aminoindan may be prepared from 4-hydroxy indanone by converting the latter to the oxide, followed by reduction1. 4-Hydroxy indanone may be prepared from dihydrocoumarin.3

Quellen und Nachweise

ORD-Eintrag
ord-ac25978d68b94785a996291f8bc81a7c
Quelldatensatz
uspto-grants-2001_10
Patentnummer
US06303650B1

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