Thionyl Chloride → 6-(4-Fluorobenzyl)-4-methoxy-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridine-1-carbonyl chloride

HRID 1817304Notes

Reaction equation

HRID 1817304 reaction equation
[F:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][N:7]2[CH2:16][CH2:15][C:14]3[C:13]([C:17](O)=[O:18])=[N:12][CH:11]=[C:10]([O:20][CH3:21])[C:9]=3[C:8]2=[O:22])=[CH:4][CH:3]=1.S(Cl)([Cl:27])=O>>[F:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][N:7]2[CH2:16][CH2:15][C:14]3[C:13]([C:17]([Cl:27])=[O:18])=[N:12][CH:11]=[C:10]([O:20][CH3:21])[C:9]=3[C:8]2=[O:22])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 690589806-(4-Fluorobenzyl)-4-methoxy-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridine-1-carboxylic acid

Product 1

HCID 866139046-(4-Fluorobenzyl)-4-methoxy-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridine-1-carbonyl chloride

Procedure

A solution of 6-(4-fluorobenzyl)-4-methoxy-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridine-1-carboxylic acid (1.11 g, 3.36 mmol) in thionyl chloride (0.4 g, 3.36 mmol) was heated to 110° C. After 0.5 hours, the product mixture was concentrated under vacuum. The residue was suspended in toluene, evaporated, then suspended in chloroform and evaporated to give the title compound. The product was assayed by quenching in methanol solution to produce the methyl ester. ES MS M+1=345 (methyl ester forms after quench in methanol)

Workup

  1. concentrationthe product mixture was concentrated under vacuum
  2. customevaporated
  3. customevaporated

Sources & evidence

ORD record
ord-9d036335e0be4003a3a6fc3ca6d473e3
Source dataset
uspto-grants-2009_10
Patent number
US07598264B2

Reaction notes

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