Water → 6-Bromo-1,8-naphthyridin-2(1H)-one

HRID 2097203Notes

Reaction equation

HRID 2097203 reaction equation
[NH2:1][C:2]1[C:7](/[CH:8]=[CH:9]/[C:10](OC(C)(C)C)=[O:11])=[CH:6][C:5]([Br:17])=[CH:4][N:3]=1.C[O-].[Na+].O>CO>[Br:17][C:5]1[CH:6]=[C:7]2[C:2](=[N:3][CH:4]=1)[NH:1][C:10](=[O:11])[CH:9]=[CH:8]2

Participants

5

Reactant 3

HCID 962WaterHCID 10942334Sodium MethoxideHCID 59277590HCID 59277590, compound

Product 1

HCID 125201446-Bromo-1,8-naphthyridin-2(1H)-oneYield 93.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of (E)-tert-butyl 3-(2-amino-5-bromopyridin-3-yl)acrylate (2.5 g, 8.35 mmol) in anhydrous methanol (50 mL) was treated with sodium methoxide (8.5 mL of a 4.9 M solution, 41.75 mmol). The solution was heated at reflux for 2 h then cooled to room temperature. The mixture was cooled in an ice-H2O bath and treated with H2O (100 mL) under rapid stirring to give a precipitate. The solid was filtered and washed with H2O (20 mL). The filtrate was neutralized with 1 M HCl(aq) to form a precipitate. The solid was filtered and washed with H2O (20 mL). The solids were combined and dried under reduced pressure to give an off-white solid (1.75 g, 93%). NMR (300 MHz, DMSO-d6) δ 8.43 (d, 1H, J=2.5 Hz), 8.06 (d, 111, J=2.5 Hz), 7.60 (d, 1H, J=9.1 Hz), 6.44 (d, 1H, J=9.1 Hz); ESI MS m/z 225 (100%); 227 (100%) [C8H5N2OBr+H]+

Workup

  1. temperatureThe solution was heated
  2. temperatureat reflux for 2 h
  3. temperatureThe mixture was cooled in an ice-H2O bath
  4. customto give a precipitate
  5. filtrationThe solid was filtered
  6. washwashed with H2O (20 mL)
  7. customto form a precipitate
  8. filtrationThe solid was filtered
  9. washwashed with H2O (20 mL)
  10. customdried under reduced pressure

Sources & evidence

ORD record
ord-90142c69244b463aa9df5fe24106dfda
Source dataset
uspto-grants-2013_05
Patent number
US08450307B2

Reaction notes

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