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

HRID 128634

反応式

[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

参加物

実験手順

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).

後処理

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

出典と根拠

ORDレコード: ord-e25a5979be754341adcd7bb4818aa142
出典データセット: uspto-grants-1995_11
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US05464781

反応式

参加物

反応物 2

生成物 1

試薬・触媒・溶媒 1

実験手順

後処理

出典と根拠

関連ノート