1-Naphthol → 1-Chloro-4-morpholin-4-yl-2-naphthol

HRID 54600

Reaktionsgleichung

Reaktionsgleichung von HRID 54600
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[OH:11].C1C=CC2C(=CC=CC=2O)C=1.[Cl:23]Cl.C(N(CC)CC)C.[NH:32]1[CH2:37][CH2:36][O:35][CH2:34][CH2:33]1>C1(C)C=CC=CC=1>[Cl:23][C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([N:32]2[CH2:37][CH2:36][O:35][CH2:34][CH2:33]2)=[CH:3][C:2]=1[OH:11]

Komponenten

7

Edukt 5

HCID 70051-NaphtholHCID 8083MorpholineHCID 8471TriethylamineHCID 86632-NaphtholHCID 24526Chlorine

Produkt 1

HCID 6096921-Chloro-4-morpholin-4-yl-2-naphtholAusbeute 109,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel2×

Versuchsvorschrift

2-Naphthol (28.8 g; 0.200 mol) was dissolved in toluene (200 ml) by warming. The pale brown solution was cooled and vigorously stirred until the naphthol began to precipitate and chlorine (31.29 g;0.442 mol) was then passed through the solution at approximately 2.5-3.0 g/min followed immediately by nitrogen gas. The resulting amber solution was treated firstly with triethylamine (24.68 g;0.244 mol) in one portion and then with a solution of morpholine (17.40 g;0.20 mol) in toluene (180 ml) dropwise over 1.5 hours keeping the temperature at 15°-20° C. The resulting brown mixture was filtered to remove triethylamine hydrochloride as a white amorphous solid. The toluene filtrate was washed with water, dried and evaporated to give 1-chloro-4-morpholino-2-naphthol as a brown viscous oil (57.76 g). Purification by chromatography over silica (eluent: 15% ethyl acetate in toluene) gave the product as an off-white solid (34.37 g;65%). Further purification by crystallisation from toluene gave the product as a white solid, m.pt. 163°-65° C. ##STR18## (b) 4-Morpholino-2-naphthol

Aufarbeitung

  1. temperatureby warming
  2. temperatureThe pale brown solution was cooled
  3. customto precipitate
  4. customat 15°-20° C
  5. filtrationThe resulting brown mixture was filtered
  6. customto remove triethylamine hydrochloride as a white amorphous solid
  7. washThe toluene filtrate was washed with water
  8. customdried
  9. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-cedecce0ec71427799fa409bfaf3db88
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05623005

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