Dimethylformamide → HCID 14676216, compound

HRID 1266912Notes

Reaction equation

HRID 1266912 reaction equation
[NH2:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][N:3]=1.CN(C)C=O.C(=O)([O-])[O-].[K+].[K+].[CH2:20](Br)[CH2:21][CH2:22][CH3:23]>C(OCC)(=O)C.O>[NH2:1][C:2]1[C:7]([O:8][CH2:20][CH2:21][CH2:22][CH3:23])=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 8002Butyl bromideHCID 11430Potassium CarbonateHCID 281142-Amino-3-Hydroxypyridine

Product 1

HCID 14676216HCID 14676216, compoundYield 41.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

A reaction flask was loaded with 2-amino-3-hydroxypyridine (8 g), dimethylformamide (DMF) (50 ml), and anhydrous potassium carbonate (12 g), and the temperature was raised up to 50° C. with stirring, followed by dropwise addition of n-butylbromide (11.9 g) to the flask in 4 hours with stirring. Then, the mixture was stirred at 60° C. for 2 hours. The heating was stopped, and water (200 ml) was added to the mixture. Ethyl acetate was added to the mixture and the mixture was stirred, followed by collecting the ethyl acetate layer with a separating funnel. The layer was condensed by an evaporator to precipitate crystals, and then the crystals were broken up with hexane. The crystals were filtrated for collection and dried to give crystals of 2-amino-3-butoxypyridine (5 g).

Workup

  1. stirringwith stirring
  2. stirringThen, the mixture was stirred at 60° C. for 2 hours
  3. stirringthe mixture was stirred
  4. customby collecting the ethyl acetate layer with a separating funnel
  5. customcondensed
  6. customby an evaporator
  7. customto precipitate crystals
  8. filtrationThe crystals were filtrated for collection
  9. customdried

Sources & evidence

ORD record
ord-f7da86e1779840c7a8e2e0f3ad382262
Source dataset
uspto-grants-2003_04
Patent number
US06551682B1

Reaction notes

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