Dimethylformamide → HCID 178479697, compound

HRID 1730266Notes

Reaction equation

HRID 1730266 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][N:10]=2)[N:5]=[CH:4][C:3]=1[C:12]([OH:14])=O.CN(C)C=O.S(Cl)([Cl:22])=O>C1C=CC=CC=1>[ClH:22].[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][N:10]=2)[N:5]=[CH:4][C:3]=1[C:12]([Cl:22])=[O:14]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 178524722HCID 178524722, compound

Product 1

HCID 178479697HCID 178479697, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

4-Hydroxy-1,5-naphthyridine-3-carboxylic acid was added to a mixture of 0.73 g of dimethylformamide and 1.56 g of thionyl chloride in benzene withstirring, and stirring was continued at 40° - 85° C for 3 hours. The precipitated crystals were collected by filtration, washed withbenzene and dried under reduced pressure to give 2.37 g of 4-hydroxy-1,5-naphthyridine-3-carbonyl chloride hydrochloride. Purity (determined by NMR analysis after esterification), 96.3 %.

Workup

  1. filtrationThe precipitated crystals were collected by filtration
  2. washwashed withbenzene and
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-1fb70a64e2a3469894560bb5bec7c154
Source dataset
uspto-grants-1976_11
Patent number
US03992371

Reaction notes

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