Aluminum(III) Chloride → 6-Hydroxy-4-(4-methoxyanilino)-7-methyl-1,8-naphthyridine-3-carboxylic acid hemihydrate

HRID 128634

Reaktionsgleichung

Reaktionsgleichung von HRID 128634
[CH3:1][O:2][C:3]1[CH:28]=[CH:27][C:6]([NH:7][C:8]2[C:17]3[C:12](=[N:13][C:14]([CH3:21])=[C:15]([O:18]CC)[CH:16]=3)[N:11]=[CH:10][C:9]=2[C:22]([O:24]CC)=[O:23])=[CH:5][CH:4]=1.[Cl-].[Al+3].[Cl-].[Cl-]>ClCCl>[OH2:2].[OH:18][C:15]1[CH:16]=[C:17]2[C:12](=[N:13][C:14]=1[CH3:21])[N:11]=[CH:10][C:9]([C:22]([OH:24])=[O:23])=[C:8]2[NH:7][C:6]1[CH:27]=[CH:28][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1.[OH:18][C:15]1[CH:16]=[C:17]2[C:12](=[N:13][C:14]=1[CH3:21])[N:11]=[CH:10][C:9]([C:22]([OH:24])=[O:23])=[C:8]2[NH:7][C:6]1[CH:27]=[CH:28][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1

Komponenten

4

Edukt 2

HCID 6451240Aluminum(III) ChlorideHCID 9907935Ethyl 6-ethoxy-4-(4-methoxyanilino)-7-methyl-1,8-naphthyridine-3-carboxylate

Produkt 1

HCID 676248076-Hydroxy-4-(4-methoxyanilino)-7-methyl-1,8-naphthyridine-3-carboxylic acid hemihydrate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A mixture of ethyl 4-(4-methoxyanilino)-6-ethoxy-7-methyl-1,8-naphthyridine-3-carboxylate (2.9 g) in dichloromethane (45 ml) was added rapidly to a suspension of powdered anhydrous aluminium chloride (12.8 g) in dichloromethane (115 ml) with stirring. The mixture was stirred for 24 hours at ambient temperature and then poured into ice/water. The mixture was stirred for 30 minutes then filtered. The residue was basified and partitioned between dichloromethane and water. The aqueous layer was evaporated to dryness. The residue was dissolved in propan-2-ol (150 ml) and then purified by column chromatography to give 6-hydroxy-4-(4-methoxyanilino)-7-methyl-1,8-naphthyridine-3-carboxylic acid hemihydrate, m.p. 267°-268° C. (with decomposition).

Aufarbeitung

  1. stirringThe mixture was stirred for 24 hours at ambient temperature
  2. stirringThe mixture was stirred for 30 minutes
  3. filtrationthen filtered
  4. custompartitioned between dichloromethane and water
  5. customThe aqueous layer was evaporated to dryness
  6. dissolutionThe residue was dissolved in propan-2-ol (150 ml)
  7. custompurified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-e25a5979be754341adcd7bb4818aa142
Quelldatensatz
uspto-grants-1995_11
Patentnummer
US05464781

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