Hydrochloric Acid → (7-Bromo-1,5-naphthyridin-3-yl)acetaldehyde

HRID 273242Notes

Reaction equation

HRID 273242 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[N:9][CH:8]=[C:7]([CH:12]=[CH:13][O:14]CC)[CH:6]=2.Cl.[OH-].[Na+]>C1COCC1.C(Cl)Cl>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([CH2:12][CH:13]=[O:14])[CH:8]=[N:9]2)=[N:4][CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 670823433-Bromo-7-[2-ethoxyvinyl]-1,5-naphthyridine

Product 1

HCID 21043926(7-Bromo-1,5-naphthyridin-3-yl)acetaldehydeYield 95%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of the product from Example 153C (0.25 g, 0.89 mmol) in 15 mL of THF was added 1.5 mL of HCl (6N). The mixture was heated to reflux for 5 hr, cooled and the pH adjusted to 8.0 with NaOH. The mixture was diluted with 75 mL of CH2Cl2 and washed successively with a saturated solution of sodium bicarbonate, brine and water. The organic layer was dried over sodium sulfate, filtered and evaporated under reduced pressure to give the desired product in 95% yield. 1H NMR (CDCl3, 300 MHz) δ 3.75 (m, 2H), 8.25 (m, 1H), 8.60 (m, 1H), 8.85 (m, 1H), 9.00 (m, 1H), 9.90 (s, 1H). MS (ESI) [M+H]+ at 252.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 5 hr
  3. temperaturecooled
  4. washwashed successively with a saturated solution of sodium bicarbonate, brine and water
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-4b6b344de2b8482d890d3bb7fe4192c9
Source dataset
uspto-grants-2008_11
Patent number
US07456196B2

Reaction notes

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