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Sodium borohydride → 6-Methyl-N4-(2-methylpropyl)-N2, N2-bis(phenylmethyl)pyridine-2,3,4-triamine

HRID 263719
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 263719
[BH4-].[Na+].[CH3:3][C:4]1[N:9]=[C:8]([N:10]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:7]([N+:25]([O-])=O)=[C:6]([NH:28][CH2:29][CH:30]([CH3:32])[CH3:31])[CH:5]=1>CO.C(Cl)Cl.O.[Ni](Cl)Cl>[CH3:3][C:4]1[N:9]=[C:8]([N:10]([CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:7]([NH2:25])=[C:6]([NH:28][CH2:29][CH:30]([CH3:32])[CH3:31])[CH:5]=1
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Komponenten

6

Edukt 2

HCID 4311764Sodium borohydride2×HCID 540930236-methyl-N4-(2-methylpropyl)-3-nitro-N2, N2-bis(phenylmethyl)pyridine-2,4-diamine

Produkt 1

HCID 538812726-Methyl-N4-(2-methylpropyl)-N2, N2-bis(phenylmethyl)pyridine-2,3,4-triamineAusbeute 85,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

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

Versuchsvorschrift

Sodium borohydride (585 mg, 16 mmole) was added to a solution of nickel (II) chloride hydrate (1.02 g, 4.3 mmole) in methanol (100 mL). The addition caused a black solid to form along with gas evolution. The resulting heterogeneous mixture was stirred at ambient temperature for 30 minutes. A solution containing 6-methyl-N4 -(2-methylpropyl)-3-nitro-N2, N2 -bis(phenylmethyl)pyridine-2,4-diamine (3.47 g, 8.6 mmole) in methylene chloride (20 mL) was added followed by the addition of sodium borohydride (1.37 g, 36 mmole). The reaction mixture was stirred at ambient temperature for about 30 minutes then eluted through a layer of silica gel with a methanol/methylene chloride mixture. The filtrate was concentrated under vacuum. The resulting residue was partitioned between ethyl acetate and water. The ethyl acetate layer was separated, dried with magnesium sulfate and concentrated under vacuum to provide 2.74 g of the desired product as a green foam.

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 30 minutes
  5. washthen eluted through a layer of silica gel with a methanol/methylene chloride mixture
  6. concentrationThe filtrate was concentrated under vacuum
  7. customThe resulting residue was partitioned between ethyl acetate and water
  8. customThe ethyl acetate layer was separated
  9. dry with materialdried with magnesium sulfate
  10. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-42a2b14812b04f67bb95c1b179e2b081
Quelldatensatz
uspto-grants-1997_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05644063

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