2-Amino-3-Hydroxypyridine → 2-(Chloromethyl)(1,3)oxazolo(4,5-b)pyridine

HRID 1253348

Reaction equation

HRID 1253348 reaction equation
[NH2:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[Cl:9][CH2:10][C:11](OCC)(OCC)OCC>COCCOCCOC>[Cl:9][CH2:10][C:11]1[O:8][C:7]2[C:2]([N:1]=1)=[N:3][CH:4]=[CH:5][CH:6]=2

Participants

4

Reactant 2

HCID 281142-Amino-3-HydroxypyridineHCID 3059222-Chloro-1,1,1-triethoxyethane

Product 1

HCID 27645692-(Chloromethyl)(1,3)oxazolo(4,5-b)pyridine

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Procedure

The commercially available 2-amino-3-hydroxypyridine (5.0 g) and diglyme (30 ml) were heated at 125° C. to obtain a solution. To this solution was added 2-chloro-1,1,1-triethoxyethane (9.9 g) and the mixture was held at 125° for 1 hour. The solution was cooled to room temperature and then decanted to remove a black byproduct residue. The filtrate was diluted with water (50 ml) and the resulting yellow precipitate was collected (1.5 g). A small sample was crystallized from isopropanol (m.p. 115°-118° C.).

Workup

  1. customto obtain a solution
  2. customdecanted
  3. customto remove a black byproduct residue
  4. additionThe filtrate was diluted with water (50 ml)
  5. customthe resulting yellow precipitate was collected (1.5 g)
  6. customA small sample was crystallized from isopropanol (m.p. 115°-118° C.)

Sources & evidence

ORD record
ord-a776109fe3c24b82833cdd246df189d5
Source dataset
uspto-grants-1988_05
Patent number
US04748280

Linked notes

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