2-Hydroxy-1-naphthaldehyde → 2-(5-carboxy-2-benzoxazolyl)-3H-naphtho[2,1-b]pyran-3-one

HRID 329705

Reaktionsgleichung

Reaktionsgleichung von HRID 329705
[OH:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]=1[CH:12]=O.C([O:16][C:17]([CH2:19][C:20]1[O:21][C:22]2[CH:28]=[CH:27][C:26]([C:29]([OH:31])=[O:30])=[CH:25][C:23]=2[N:24]=1)=O)C>N1CCCCC1.C(O)(=O)C.C(O)C>[C:29]([C:26]1[CH:27]=[CH:28][C:22]2[O:21][C:20]([C:19]3[C:17](=[O:16])[O:1][C:2]4[CH:11]=[CH:10][C:9]5[C:4]([C:3]=4[CH:12]=3)=[CH:5][CH:6]=[CH:7][CH:8]=5)=[N:24][C:23]=2[CH:25]=1)([OH:31])=[O:30]

Komponenten

6

Edukt 2

HCID 128192-Hydroxy-1-naphthaldehydeHCID 198714242-Ethoxycarbonylmethyl-5-carboxybenzoxazole

Produkt 1

HCID 198714232-(5-carboxy-2-benzoxazolyl)-3H-naphtho[2,1-b]pyran-3-oneAusbeute 56 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidKatalysatorHCID 8082PiperidineKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 2-hydroxy-1-naphthaldehyde (1.72 g, 0.01 mol), 2-ethoxycarbonylmethyl-5-carboxybenzoxazole (2.49 g, 0.01 mol), ethanol (30 mL), piperidine (10 drops), and acetic acid (5 drops) is heated at reflux for 3 hours. After cooling the reaction mixture is filtered to isolate the yellow fluorescent product which is then washed with ethanol and dried in air to yield 2.0 g (56% of theory) of 2-(5-carboxy-2-benzoxazolyl)-3H-naphtho[2,1-b]pyran-3-one having the structure ##STR19##

Aufarbeitung

  1. temperatureis heated
  2. temperatureat reflux for 3 hours
  3. temperatureAfter cooling the reaction mixture
  4. filtrationis filtered
  5. customto isolate the yellow fluorescent product which
  6. washis then washed with ethanol
  7. customdried in air

Quellen und Nachweise

ORD-Eintrag
ord-f256b0f0768d4dde922bb36ecab302f2
Quelldatensatz
uspto-grants-1990_01
Patentnummer
US04892923

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