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

HRID 128634

Reaction equation

HRID 128634 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-e25a5979be754341adcd7bb4818aa142
Source dataset
uspto-grants-1995_11
Patent number
US05464781

Linked notes

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