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

HRID 3923

Reaction equation

HRID 3923 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-3b3a232422e4466d95c7b4b7201b4772
Source dataset
uspto-grants-1988_02
Patent number
US04723010

Linked notes

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