Hydrochloric Acid → 1-butyl-4-hydroxy-1,8-naphthyridin-2(1H)-one

HRID 601302Notes

Reaction equation

HRID 601302 reaction equation
[CH2:1]([N:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][N:13]=2)[C:8]([OH:15])=[C:7](C(OCC)=O)[C:6]1=[O:21])[CH2:2][CH2:3][CH3:4].Cl>[OH-].[Na+]>[CH2:1]([N:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][N:13]=2)[C:8]([OH:15])=[CH:7][C:6]1=[O:21])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 54692485HCID 54692485, compound

Product 1

HCID 670640031-butyl-4-hydroxy-1,8-naphthyridin-2(1H)-oneYield 101.4%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
11 °C

Procedure

A slurry of the product of Example 89A (3.24 g, 11.16 mmol) in 2 N sodium hydroxide (100 mL) was heated at reflux for 3 hours, cooled to 11° C. and treated dropwise with concentrated hydrochloric acid to a constant pH of 3. The resulting white solid was collected by filtration, washed with water and dried to give the title compound (2.47 g, quantitative). MS (APCI+) m/z 219 (M+H)+. 1H NMR (300 MHz, DMSO-d6) δ ppm 0.90 (t, J=7.35 Hz, 3 H) 1.32 (m, 2 H) 1.57 (m, 2 H) 4.31 (m, 2 H) 5.89 (s, 1 H) 7.27 (dd, J=7.72, 4.78 Hz, 1 H) 8.23 (dd, J=7.72, 1.84 Hz, 1 H) 8.64 (dd, J=4.78, 1.84 Hz, 1 H) 11.61 (s, 1 H).

Workup

  1. temperatureat reflux for 3 hours
  2. filtrationThe resulting white solid was collected by filtration
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-daf53ed758cf418682a362cbde713ee2
Source dataset
uspto-grants-2011_03
Patent number
US07902203B2

Reaction notes

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