Hydrochloric Acid → N-(4-Hydroxyphenyl)-N-(6-hydroxy-2-naphthalenyl)acetamide

HRID 1194508

Reaktionsgleichung

Reaktionsgleichung von HRID 1194508
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[CH:15]=[C:14]([OH:19])[CH:13]=[CH:12]3)=[CH:4][CH:3]=1.CN(C)C1C=CC=CC=1.[C:29](Cl)(=[O:31])[CH3:30].Cl>C(Cl)Cl.C1COCC1>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([C:9]2[CH:18]=[CH:17][C:16]3[C:11](=[CH:12][CH:13]=[C:14]([OH:19])[CH:15]=3)[CH:10]=2)[C:29](=[O:31])[CH3:30])=[CH:4][CH:3]=1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 949N,N-DimethylanilineHCID 6367Acetyl chlorideHCID 144992086-[(4-Hydroxyphenyl)amino]-2-naphthalenol

Produkt 1

HCID 14499220N-(4-Hydroxyphenyl)-N-(6-hydroxy-2-naphthalenyl)acetamideAusbeute 10 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 830 mg (3.30 mmol) of 6-[(4-hydroxyphenyl)amino]-2-naphthalenol (prepared as described in Example 3) and 840 ul (6.60 mmol, 2 eq.) of dimethylaniline in 15 ml of dry CH2Cl2 and 5 ml of dry THF was stirred at 0° C., then 415 ul (5.80 mmol, Mallinckrodt) of acetyl chloride was added dropwise. After 50 minutes, 1N aqueous HCl was added and this was extracted with EtOAc. The organic layers were washed with 1N aqueous HCl, dried (MgSO4) and concentrated in vacuo. The aqueous layers were extracted with hot EtOAc and the organic layers were combined, dried (MgSO4) and concentrated in vacuo. Purification of all the organic phases was accomplished via flash chromatography (1:2, 1:1 EtOAc/petroleum ether) and recrystallization (aqueous MeOH) afforded 97 mg (10%) of title compound as pale orange crystals: m.p. 255° C.

Aufarbeitung

  1. extractionthis was extracted with EtOAc
  2. washThe organic layers were washed with 1N aqueous HCl
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. extractionThe aqueous layers were extracted with hot EtOAc
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customPurification of all the organic phases
  9. customwas accomplished via flash chromatography (1:2, 1:1 EtOAc/petroleum ether) and recrystallization (aqueous MeOH)

Quellen und Nachweise

ORD-Eintrag
ord-b8d0f07af7ee4f67b4c748e7c8f540a2
Quelldatensatz
uspto-grants-1989_03
Patentnummer
US04814454

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