Methyl iodide → 8-Amino-2-naphthalenol

HRID 719181

Reaktionsgleichung

Reaktionsgleichung von HRID 719181
[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH:10]=[C:9](S(O)(=O)=O)[CH:8]=[CH:7]2.[NH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[C:21]2[C:26]=1[CH:25]=[C:24]([OH:27])[CH:23]=[CH:22]2.[H-].[Na+].CI>CN(C)C=O.O>[NH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[C:21]2[C:26]=1[CH:25]=[C:24]([OH:27])[CH:23]=[CH:22]2.[CH3:24][O:27][C:9]1[CH:10]=[C:11]2[C:6]([CH:5]=[CH:4][CH:3]=[C:2]2[NH2:1])=[CH:7][CH:8]=1

Komponenten

8

Edukt 4

HCID 6328Methyl iodideHCID 83588-Amino-2-naphthalenolHCID 8386Cleve's acidHCID 24758Sodium hydride

Produkt 2

HCID 83588-Amino-2-naphthalenolHCID 2358177-Methoxynaphthalen-1-amine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

8-Amino-naphthalen-2-ol was prepared from 8-amino-2-naphthalenesulphonic acid (commercially available) according to the literature (J. Org. Chem. 1949, p351). To a solution of 8-amino-naphthalen-2-ol (8.00 g) in dry N,N-dimethylformamide (80 mL) was added sodium hydride (60% dispersion in mineral oil, 3.2 g) carefully. After stirring for 4 hours the reaction mixture was cooled in an ice bath and methyl iodide (3.13 mL) was added dropwise. The reaction mixture was then stirred at room temperature for 3 days. Water (10 mL) was then added and the volatiles were removed in vacuo. The residue was dissolved in chloroform, washed with water, dried (MgSO4) and the solvent removed in vacuo to yield a dark oil. This was purified using flash chromatography (chloroform) to yield 7-methoxy-naphthalen-1-ylamine as a dark brown liquid (2.92 g).

Aufarbeitung

  1. temperaturewas cooled in an ice bath
  2. stirringThe reaction mixture was then stirred at room temperature for 3 days
  3. customthe volatiles were removed in vacuo
  4. dissolutionThe residue was dissolved in chloroform
  5. washwashed with water
  6. dry with materialdried (MgSO4)
  7. customthe solvent removed in vacuo
  8. customto yield a dark oil
  9. customThis was purified

Quellen und Nachweise

ORD-Eintrag
ord-d39c13159e5342e598803700f91173f1
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07132419B2

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