Benzene → HCID 178479697, compound

HRID 1415110Notes

Reaction equation

HRID 1415110 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.C1C=CC=CC=1.S(Cl)([Cl:23])=O>CN(C)C=O>[ClH:23].[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:23])=[O:14]

Participants

5

Reactant 3

HCID 241BenzeneHCID 24386Thionyl ChlorideHCID 178524722HCID 178524722, compound

Product 1

HCID 178479697HCID 178479697, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Hydroxy-1,5-naphthyridine-3-carboxylic acid was added to a mixture of benzene, 0.73 g of dimethylformamide and 1.56 g of thionyl chloride, and the resulting mixture was stirred at 40° to 85° C for 3 hours. The precipitated crystals were collected by filtration, washed with benzene and dried under reduced pressure to give 2.37 g of 4-hydroxy-1,5-naphthyridine-3-carbonyl chloride hydrochloride as crystals. Purity (determined by NMR analysis as the ester form obtained by further alcoholysis), 96.3%.

Workup

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

Sources & evidence

ORD record
ord-386d22708dd14f1a989221476e25d264
Source dataset
uspto-grants-1977_01
Patent number
US04003887

Reaction notes

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