Chloroacetyl chloride → 4-Chloroacetamido-3-hydroxypyridine

HRID 266915Notes

Reaction equation

HRID 266915 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[OH:8].[Cl:9][CH2:10][C:11](Cl)=[O:12]>>[Cl:9][CH2:10][C:11]([NH:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[OH:8])=[O:12]

Participants

3

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 27624194-Amino-3-hydroxypyridine

Product 1

HCID 190316634-Chloroacetamido-3-hydroxypyridine

Procedure

A solution of 4-amino-3-hydroxypyridine (7 g, 0.06 mol) and chloroacetyl chloride (50 ml) was refluxed for 2 hours, cooled and the excess solvent was removed by vacuum distillation. The crude material was dissolved in water, neutralized with Na2CO3 and the solid precipitated filtered and air dried to give the desired product, m.p. 155°-158° C. The structural assignment was supported by the proton NMR spectrum.

Workup

  1. temperaturecooled
  2. customthe excess solvent was removed by vacuum distillation
  3. dissolutionThe crude material was dissolved in water
  4. customthe solid precipitated
  5. filtrationfiltered
  6. customair dried

Sources & evidence

ORD record
ord-0e717692545847bf99de662dd998060e
Source dataset
uspto-grants-1997_07
Patent number
US05652363

Reaction notes

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