Lithium Hydroxide → 8-(Aminomethyl)naphthalene-2-carboxylic acid

HRID 376808Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 376808
[NH2:1][CH2:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[CH:11]=[C:10]([C:13]([O:15]C)=[O:14])[CH:9]=[CH:8]2.[OH-].[Li+]>O1CCCC1>[NH2:1][CH2:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[CH:11]=[C:10]([C:13]([OH:15])=[O:14])[CH:9]=[CH:8]2

Komponenten

4

Edukt 2

HCID 3939Lithium Hydroxide2×HCID 14731550Methyl 8-(aminomethyl)naphthalene-2-carboxylate

Produkt 1

HCID 147565638-(Aminomethyl)naphthalene-2-carboxylic acidAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Part C--To a solution of methyl 8-aminomethyl-2-naphthoate (0.75 g, 0.0035 mol) in dry tetrahydrofuran (50 mL), cooled to 0° C., was added a solution of lithium hydroxide (0.5 M, 5.83 mL). All was stirred at ambient temperature over 20 hours. Another aliquot of lithium hydroxide was added and all was stirred for an additional 20 hours. The solid was collected and the filtrate was evaporated to dryness under reduced pressure. The solids were triturated with diethyl ether to give 8-aminomethyl-2-naphthoic acid (0.67 g, 0.0033 mol, 95%) as a white solid. mp=223-225° C.; 1H NMR (DMSO) d 8.6 (s, 1H), 8.1-7.9 (m, 1H), 7.8-7.7 (m, 4H), 7.55-7.5 (m, 1H), 7,45-7.35 (m, 2H), 4.2 (s, 2H).

Aufarbeitung

  1. stirringall was stirred for an additional 20 hours
  2. customThe solid was collected
  3. customthe filtrate was evaporated to dryness under reduced pressure
  4. customThe solids were triturated with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-2cad2836343e484bb41e39c9e644633b
Quelldatensatz
uspto-grants-2000_02
Patentnummer
US06022523

Notizen zur Reaktion

Wird geladen…