3-(Nitromethyl)-1,2-dihydronaphthalene → 1,2,3,4-Tetrahydronaphthalen-2-ylmethanamine

HRID 1029747Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1029747
[N+:1]([CH2:4][C:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=1)([O-])=O.[H][H]>CO.[Pd]>[NH2:1][CH2:4][CH:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6]1

Komponenten

5

Edukt 2

HCID 153234983-(Nitromethyl)-1,2-dihydronaphthaleneHCID 178418361HCID 178418361, Verbindung2×

Produkt 1

HCID 157186321,2,3,4-Tetrahydronaphthalen-2-ylmethanamine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

2-Nitromethyl-3,4-dihydronaphthalene (XXXV) (25 g) and 20% Pd/C (1.0 g) were combined in MeOH (200 ml) and shaken in a Parr hydrogenator at 3 atmospheres hydrogen pressure for 24 hours, by which time the theoretical amount of hydrogen (4 equivalents) had been absorbed. Removal of the catalyst and solvent left an oil (24 g) which was converted to its HCl salt by solution in MeOH and addition of concentrated HCl. The product, compound XXXI.HCl, was recrystallized from 2-propanol, yielding a white solid, m.p. 230° (dec.). Its elemental analysis and NMR spectrum were consistent with the structure indicated.

Aufarbeitung

  1. customhad been absorbed
  2. customRemoval of the catalyst and solvent
  3. waitleft an oil (24 g) which
  4. additionaddition of concentrated HCl
  5. customThe product, compound XXXI.HCl, was recrystallized from 2-propanol
  6. customyielding a white solid, m.p. 230° (dec.)

Quellen und Nachweise

ORD-Eintrag
ord-c4630e90414c4338a748da2fff6030dc
Quelldatensatz
uspto-grants-1992_04
Patentnummer
US05102914

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