Aluminum(III) Chloride → HCID 12875022, compound

HRID 847775Notes

Reaction equation

HRID 847775 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].C([O:7][C:8]1[CH:9]=[C:10]2[C:15](=[N:16][C:17]=1[CH:18]=[O:19])[N:14]([CH2:20][CH3:21])[CH:13]=[C:12]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:11]2=[O:27])C>ClCCl>[CH2:20]([N:14]1[C:15]2[C:10](=[CH:9][C:8]([OH:7])=[C:17]([CH:18]=[O:19])[N:16]=2)[C:11](=[O:27])[C:12]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:13]1)[CH3:21]

Participants

4

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 12875021HCID 12875021, compound

Product 1

HCID 12875022HCID 12875022, compoundYield 95.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To 500 ml of dichloromethane was added 53 g of pulverized aluminium chloride and stirred at room temperature for 1 hour. To the above mixture, a solution of 25.0 g of ethyl 1,4-dihydro-6-ethoxy-1-ethyl-7-formyl-4-oxo-1,8-naphthyridine-3-carboxylate dissolved in 200 ml of dichloromethane was slowly added dropwise. After the resulting mixture was stirred at room temperature for 3 hours, ice water was added to the reaction mixture and allowed to separate into two layers. The aqueous layer was extracted with chloroform and the chloroform extract and the organic layer were combined, and washed with water, dried and evaporated in vacuo to obtain 21.8 g of ethyl 1,4-dihydro-1-ethyl-7-formyl-6-hydroxy-4-oxo-1,8-naphthyridine-3-carboxylate (Compound IX where R1 =R3 =C2H5), m.p. 243°-245° C.

Workup

  1. additionwas slowly added dropwise
  2. stirringAfter the resulting mixture was stirred at room temperature for 3 hours
  3. customto separate into two layers
  4. extractionThe aqueous layer was extracted with chloroform
  5. extractionthe chloroform extract
  6. washwashed with water
  7. customdried
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-4e931b0dcaf446ac99d4d39cf74c27fc
Source dataset
uspto-grants-1981_10
Patent number
US04293695

Reaction notes

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