Thionyl Chloride → HCID 12818608, compound

HRID 1703120Notes

Reaction equation

HRID 1703120 reaction equation
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH3:12])[N:10]=2)[C:5](O)=[C:4]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:3]1=[O:19].S(Cl)([Cl:22])=O>>[Cl:22][C:5]1[C:6]2[C:11](=[N:10][C:9]([CH3:12])=[CH:8][CH:7]=2)[N:2]([CH3:1])[C:3](=[O:19])[C:4]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 54696181Ethyl 4-hydroxy-1,7-dimethyl-2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxylate

Product 1

HCID 12818608HCID 12818608, compound

Procedure

A stirred mixture of 1 g. of 1,2-dihydro-1,7-dimethyl-4-hydroxy-2-oxo-1,8-naphthyridine-3-carboxylic acid, ethyl ester in 25 ml. of thionyl chloride was heated under reflux for 5 hours. The thionyl chloride was removed in a rotary evaporator and the residue was triturated with 10 ml. of ethyl acetate. The insoluble material was collected to give 0.8 g. of material. A small amount of this solid was recrystallized from ethyl acetate to give the analytical sample, m.p. 180°-184° C. of 4-chloro-1,2-dihydro-1,7-dimethyl-2-oxo-1,8-naphthyridine-3-carboxylic acid, ethyl ester.

Workup

  1. additionA stirred mixture of 1 g
  2. temperatureunder reflux for 5 hours
  3. customThe thionyl chloride was removed in a rotary evaporator
  4. customthe residue was triturated with 10 ml
  5. customThe insoluble material was collected
  6. customto give 0.8 g
  7. customA small amount of this solid was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-db6bf463194c414baa4665caec186aa3
Source dataset
uspto-grants-1982_09
Patent number
US04350817

Reaction notes

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