Hydrochloric Acid → 4-(3-bromophenyl)-6-(4-chlorobenzoyl)-1-methyl-1,8-naphthyridin-2(1H)-one

HRID 1799166Notes

Reaction equation

HRID 1799166 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[C:12](=[N:13][CH:14]=[C:15]([C:18]4([C:23]5[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=5)OCC[O:19]4)[CH:16]=3)[N:11]([CH3:30])[C:10](=[O:31])[CH:9]=2)[CH:5]=[CH:6][CH:7]=1.Cl>O1CCOCC1>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[C:12](=[N:13][CH:14]=[C:15]([C:18](=[O:19])[C:23]4[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=4)[CH:16]=3)[N:11]([CH3:30])[C:10](=[O:31])[CH:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 674285244-(3-bromophenyl)-6-(2-(4-chlorophenyl)-1,3-dioxolan-2-yl)-1-methyl-1,8-naphthyridin-2(1H)-one

Product 1

HCID 708825154-(3-bromophenyl)-6-(4-chlorobenzoyl)-1-methyl-1,8-naphthyridin-2(1H)-oneYield 88%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
70 °C

Procedure

To a solution compound H (0.4 g, 0.81 mmol) in dioxane (5 mL) was added 6 N HCl (0.5 mL) at 0° C. The mixture was heated at 70° C. for 1.5 h and cooled to RT. Dioxane was removed under reduced pressure; the reaction mixture was neutralized with saturated NaHCO3 solution and extracted with EtOAc (25 mL). The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure. The crude product was purified by column chromatography to obtain 0.32 g (88%) of compound I as off-white solid.

Workup

  1. temperaturecooled to RT
  2. customDioxane was removed under reduced pressure
  3. extractionextracted with EtOAc (25 mL)
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-85c6833e47bc450092e8a9ba389ba0fe
Source dataset
uspto-grants-2013_01
Patent number
US08343996B2

Reaction notes

Loading…