Ammonium Hydroxide → HCID 10606940, compound

HRID 1168940Notes

Reaction equation

HRID 1168940 reaction equation
Br[C:2]1[CH:3]=[C:4]([O:8][CH:9]([CH3:11])[CH3:10])[CH:5]=[N:6][CH:7]=1.[OH-].[NH4+:13]>CO.[Cu]Br>[CH:9]([O:8][C:4]1[CH:3]=[C:2]([NH2:13])[CH:7]=[N:6][CH:5]=1)([CH3:11])[CH3:10]

Participants

5

Reactant 2

HCID 14923Ammonium HydroxideHCID 105848083-Bromo-5-(propan-2-yloxy)pyridine

Product 1

HCID 10606940HCID 10606940, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 24593copper(I) bromideCatalystHCID 887MethanolSolvent

Conditions

Temperature
170 °C

Procedure

Crude 5-bromo-3-isopropoxypyridine (3.71 g, 17.18 mmol) was dissolved in methanol (46 mL) and added to concentrated ammonium hydroxide (29.7%, 14.8 M, 50 mL) and copper(I) bromide (2.46 g, 17.18 mmol) in a heavy-walled glass pressure-tube apparatus. The tube was sealed and the mixture was stirred and heated at 170° C. (oil bath temperature) for 24 h. After cooling, the solution was concentrated by rotary evaporation. Sodium carbonate solution (17.6%, 200 mL) was added, and the mixture was extracted with CH2Cl2 (4×50 mL). The combined CH2Cl2 extracts were dried (MgSO4), filtered, and concentrated by rotary evaporation to give 1.88 g (72.0%) of a brown oil.

Workup

  1. customThe tube was sealed
  2. temperatureAfter cooling
  3. concentrationthe solution was concentrated by rotary evaporation
  4. additionSodium carbonate solution (17.6%, 200 mL) was added
  5. extractionthe mixture was extracted with CH2Cl2 (4×50 mL)
  6. dry with materialThe combined CH2Cl2 extracts were dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-5be74c21cef9416baf9b31bfdd3ca492
Source dataset
uspto-grants-2003_09
Patent number
US06627648B1

Reaction notes

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