Sodium Bicarbonate → 6-Chloro-5-methyl-3-phenyl-1,7-naphthyridine

HRID 2379698Notes

Reaction equation

HRID 2379698 reaction equation
[Cl:1][C:2]1[C:7]([CH3:8])=[C:6]([CH2:9][C:10](O)([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)C(OCC)OCC)[C:5]([NH:25][C:26](=O)C(C)(C)C)=[CH:4][N:3]=1.C([O-])(O)=O.[Na+]>Cl>[Cl:1][C:2]1[C:7]([CH3:8])=[C:6]2[C:5](=[CH:4][N:3]=1)[N:25]=[CH:26][C:10]([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)=[CH:9]2

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 104114103-[2-Chloro-3-methyl-5-pivaloylamino-4-pyridyl]-1,1-diethoxy-2-hydroxy-2-phenylpropane

Product 1

HCID 99925076-Chloro-5-methyl-3-phenyl-1,7-naphthyridine

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

180.5 g (0.4 mol) of finely divided compound from Example I are intensively stirred under reflux for 5 h in 2.6 l of 2N HCl using a mechanical stirrer. The mixture is then neutralised with NaHCO3 and extracted several times with ethyl acetate, and the extracts are dried. 37.6 g of the title compound are obtained by crystallisation. Chromatography of the mother liquor (silica gel, toluene→toluene/ethyl acetate 2:1) yields a further 23.14 g of the title compound. Total yield: 60% M.p.: 136° C.

Workup

  1. extractionextracted several times with ethyl acetate
  2. customthe extracts are dried

Sources & evidence

ORD record
ord-817c21cae54f45b48cf0cea7e82f0ffc
Source dataset
uspto-grants-1994_11
Patent number
US05364855

Reaction notes

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