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Sodium borohydride → N2,N2,N4-Tris(phenylmethyl)-5,6,7,8-tetrahydroquinolin-2,3,4-triamine

HRID 1757100
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1757100
[BH4-].[Na+].[C:3]1([CH2:9][N:10]([CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:11]2[C:20]([N+:21]([O-])=O)=[C:19]([NH:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:18]3[CH2:17][CH2:16][CH2:15][CH2:14][C:13]=3[N:12]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>CO.C(Cl)Cl.O.[Ni](Cl)Cl>[C:33]1([CH2:32][N:10]([CH2:9][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:11]2[C:20]([NH2:21])=[C:19]([NH:24][CH2:25][C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[C:18]3[CH2:17][CH2:16][CH2:15][CH2:14][C:13]=3[N:12]=2)[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1
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Komponenten

6

Edukt 2

HCID 4311764Sodium borohydride2×HCID 57070605N2,N2,N4-Tris(phenylmethyl)-5,6,7,8-tetrahydro-3-nitroquinolin-2,4-diamine

Produkt 1

HCID 57018445N2,N2,N4-Tris(phenylmethyl)-5,6,7,8-tetrahydroquinolin-2,3,4-triamineAusbeute 92,9 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 16212333Nickel chloride hydrateKatalysator
HCID 887
Methanol
Lösungsmittel
HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Sodium borohydride (0.82 g, 22 mmole) was added to a solution of nickel(II) chloride hydrate (1.43 g, 6 mmole) in methanol (300 mL). The addition caused a black solid to form along with gas evolution. The resulting heterogeneous mixture was stirred at ambient temperature for about 30 minutes. A solution containing N2,N2,N4 -Tris(phenylmethyl)-5,6,7,8-tetrahydro-3-nitroquinolin-2,4-diamine (5.73 g, 12 mmole) in methylene chloride (20 mL) was added followed by 5 successive additions of sodium borohydride (0.38 g, 10 mmole each addition). The reaction mixture was stirred at ambient temperature for about 15 minutes then filtered through a layer of silica gel. The filtrate was evaporated. The residue was taken up in a minimum amount of methylene chloride then placed on a layer of silica gel. The silica gel was eluted with hexane:ethyl acetate 80:20. The organic phase was collected then evaporated to provide 5.0 g of the desired product as a green oil.

Aufarbeitung

  1. additionThe addition
  2. customto form along with gas evolution
  3. additionwas added
  4. stirringThe reaction mixture was stirred at ambient temperature for about 15 minutes
  5. filtrationthen filtered through a layer of silica gel
  6. customThe filtrate was evaporated
  7. washThe silica gel was eluted with hexane:ethyl acetate 80:20
  8. customThe organic phase was collected
  9. customthen evaporated

Quellen und Nachweise

ORD-Eintrag
ord-ca15d9f5fa4b48afb06215ae3e0eee1e
Quelldatensatz
uspto-grants-1995_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05444065

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