Water → HCID 21286374, compound

HRID 2231195Notes

Reaction equation

HRID 2231195 reaction equation
[NH2:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[H-].[Na+].Cl[CH2:12][C:13]1[S:14][CH:15]=[CH:16][C:17]=1[CH3:18].O>CN(C)C=O>[NH2:1][C:2]1[C:7]([O:8][CH2:12][C:13]2[S:14][CH:15]=[CH:16][C:17]=2[CH3:18])=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 281142-Amino-3-HydroxypyridineHCID 13979509HCID 13979509, compound

Product 1

HCID 21286374HCID 21286374, compoundYield 77.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 2-amino-3-hydroxypyridine (15.18 g) in N,N-dimethylformamide (150 ml) was added portionwise a 60% dispersion of sodium hydride in mineral oil (6.06 g) with ice-cooling and stirring over a period of 10 minutes. After being stirred at 0°-5° C. for 30 minutes and then at ambient temperature for 1 hour, a solution of 2-chloromethyl-3-methylthiophene (23.9 g) in N,N-dimethylformamide (10 ml) was added dropwise to the reaction mixture. The mixture was stirred at ambient temperature for 20 hours and poured into water. The resulting precipitate was collected by filtration and dissolved in methylene chloride. The solution was treated with activated charcoal and evaporated in vacuo. The residue was crystallized from diethyl ether to give 2-amino-3-(3-methyl-2-thienylmethoxy)pyridine (23.6 g).

Workup

  1. temperaturecooling
  2. stirringAfter being stirred at 0°-5° C. for 30 minutes
  3. waitat ambient temperature for 1 hour
  4. stirringThe mixture was stirred at ambient temperature for 20 hours
  5. filtrationThe resulting precipitate was collected by filtration
  6. dissolutiondissolved in methylene chloride
  7. additionThe solution was treated with activated charcoal
  8. customevaporated in vacuo
  9. customThe residue was crystallized from diethyl ether

Sources & evidence

ORD record
ord-5e310bb4eea04c1eb2fe76a441cb25ea
Source dataset
uspto-grants-1988_11
Patent number
US04782055

Reaction notes

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