Dimethylformamide → HCID 14676218, compound

HRID 1266941Notes

Reaction equation

HRID 1266941 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+].Br[CH2:21][CH2:22][CH3:23]>CCOCC.O>[NH2:1][C:2]1[C:7]([O:8][CH2:21][CH2:22][CH3:23])=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 78401-BromopropaneHCID 11430Potassium CarbonateHCID 281142-Amino-3-Hydroxypyridine

Product 1

HCID 14676218HCID 14676218, compoundYield 24.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
50 °C

Procedure

A reaction flask was loaded with 2-amino-3-hydroxypyridine (12 g), dimethylformamide (75 ml), and potassium carbonate (18 g), and they were mixed. The temperature was raised to 50° C. To this mixture, 1-bromopropane (16.1 g) was dropwise added in 30 minutes. After stirring at 50° C. overnight, water and ether were added to the mixture, followed by stirring. The organic layer was collected from this, and washed with water, and then condensed to give 2-amino-3-propoxypyridine (4.0 g).

Workup

  1. additionwere mixed
  2. stirringby stirring
  3. customThe organic layer was collected from this, and
  4. washwashed with water
  5. customcondensed

Sources & evidence

ORD record
ord-2a6794c385fe422793d55621534dcde2
Source dataset
uspto-grants-2003_04
Patent number
US06551682B1

Reaction notes

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