Dimethylformamide → HCID 13377407, compound

HRID 638248Notes

Reaction equation

HRID 638248 reaction equation
C(Cl)(=O)C([Cl:4])=O.CN(C)C=O.O[C:13]1[C:22]2[C:17](=[C:18]([O:25][CH3:26])[N:19]=[C:20]([O:23][CH3:24])[CH:21]=2)[N:16]=[CH:15][C:14]=1[C:27]([O:29][CH2:30][CH3:31])=[O:28]>C(#N)C>[Cl:4][C:13]1[C:22]2[C:17](=[C:18]([O:25][CH3:26])[N:19]=[C:20]([O:23][CH3:24])[CH:21]=2)[N:16]=[CH:15][C:14]=1[C:27]([O:29][CH2:30][CH3:31])=[O:28]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 178469680HCID 178469680, compound

Product 1

HCID 13377407HCID 13377407, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 3.5 g of oxalyl chloride in 5 ml of dry acetonitrile is added dropwise to anhydrous dimethylformamide at -30°. After 20 minutes, 7.0 g of ethyl 4-hydroxy-6,8-dimethoxy-1,7-naphthyridine-3-carboxylate is added at -30°. Reaction temperature is kept between -20° and -30° for 30 minutes, then allowed to warm up to room temperature and evaporated to dryness. Residue is taken up in chloroform, washed with cold sodium bicarbonate aqueous solution, dried over magnesium sulfate, treated with decolorizing charcoal and evaporated to dryness to yield ethyl 4-chloro-6,8-dimethoxy-1,7-naphthyridine-3-carboxylate, m.p. 200°-210°.

Workup

  1. customReaction temperature
  2. waitis kept between -20° and -30° for 30 minutes
  3. customevaporated to dryness
  4. washwashed with cold sodium bicarbonate aqueous solution
  5. dry with materialdried over magnesium sulfate
  6. additiontreated with decolorizing charcoal
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-4aebcf21a3224174a79a6fb37da0261d
Source dataset
uspto-grants-1985_12
Patent number
US04560689

Reaction notes

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