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Isopropanol → 3-[(2,2-Dimethyl-7-methoxy-2H-chromen-5-yl)amino]-4-nitro-2-naphthalene-carboxylic acid

HRID 478689
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 478689
[NH2:1][C:2]1[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH3:15])([CH3:14])[O:7]2.Cl[C:17]1[C:18]([C:30]([OH:32])=[O:31])=[CH:19][C:20]2[C:25]([C:26]=1[N+:27]([O-:29])=[O:28])=[CH:24][CH:23]=[CH:22][CH:21]=2.C([O-])(=O)C.[K+].CC(O)C>CC([O-])=O.CC([O-])=O.[Cu+2].O.C(N(CC)CC)C>[CH3:14][C:6]1([CH3:15])[CH:5]=[CH:4][C:3]2[C:8](=[CH:9][C:10]([O:12][CH3:13])=[CH:11][C:2]=2[NH:1][C:17]2[C:18]([C:30]([OH:32])=[O:31])=[CH:19][C:20]3[C:25]([C:26]=2[N+:27]([O-:29])=[O:28])=[CH:24][CH:23]=[CH:22][CH:21]=3)[O:7]1
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Komponenten

7

Edukt 4

HCID 3776IsopropanolHCID 517044Potassium AcetateHCID 109981537-methoxy-2,2-dimethyl-2H-1-benzopyran-5-ylamineHCID 220645163-Chloro-4-nitro-2-naphthalenecarboxylic acid

Produkt 1

HCID 220645353-[(2,2-Dimethyl-7-methoxy-2H-chromen-5-yl)amino]-4-nitro-2-naphthalene-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 165397Cupric acetate monohydrateKatalysatorHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

To 3.3 g of 5-amino-7-methoxy-2,2-dimethylchromene there are added 3 g of the compound obtained in Step 3 above, 3.4 g of potassium acetate, 375 mg of Cu(OAc)2.H2O and 120 ml of 2-propanol containing 3.8 ml of triethylamine. The solution is refluxed for 5 days and is then evaporated under reduced pressure. The residue is taken up in a 1/1 mixture of dichloromethane and 1N aqueous HCl solution. After extraction of the aqueous phase, the combined organic phases are treated in customary manner. Chromatography over silica gel (dichloromethane/methanol: gradient from 0.1 to 1%) allows the expected product to be isolated.

Aufarbeitung

  1. temperatureThe solution is refluxed for 5 days
  2. customis then evaporated under reduced pressure
  3. additionThe residue is taken up in a 1/1 mixture of dichloromethane and 1N aqueous HCl solution
  4. extractionAfter extraction of the aqueous phase
  5. additionthe combined organic phases are treated in customary manner
  6. customto be isolated

Quellen und Nachweise

ORD-Eintrag
ord-b87ee55fc5804c05b593326b244e6c71
Quelldatensatz
uspto-grants-2003_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06642248B2

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