Acetic Anhydride → HCID 20030813, compound

HRID 232033Notes

Reaction equation

HRID 232033 reaction equation
[OH:1][CH2:2][CH2:3][NH:4][C:5]1[C:10]([NH2:11])=[CH:9][CH:8]=[CH:7][N:6]=1.[C:12](OC(=O)C)(=O)[CH3:13]>>[OH:1][CH2:2][CH2:3][N:4]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:10]2[N:11]=[C:12]1[CH3:13]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 157187622-[(3-Aminopyridin-2-yl)amino]ethan-1-ol

Product 1

HCID 20030813HCID 20030813, compoundYield 59%

Procedure

2-(2-Hydroxyethylamino)-3-aminopyridine (3.4 g) was dissolved in acetic anhydride (140 ml) and stirred at reflux for 15 hours. The reaction mixture was cooled and the excess of reagent removed under reduced pressure. The dark brown oil was dissolved in ethanol (100 ml), 2N sodium hydroxide (50 ml) was added and the mixture was stirred for 15 minutes. The solution was acidified to pH5 using 2N hydrochloric acid and the solvents removed under reduced pressure. The residue was chromatographed over silica eluting with 10% methanol in ethyl acetate to yield the title compound (2.32 g, 59%) as a foam.

Workup

  1. temperatureat reflux for 15 hours
  2. temperatureThe reaction mixture was cooled
  3. customthe excess of reagent removed under reduced pressure
  4. dissolutionThe dark brown oil was dissolved in ethanol (100 ml)
  5. addition2N sodium hydroxide (50 ml) was added
  6. stirringthe mixture was stirred for 15 minutes
  7. customthe solvents removed under reduced pressure
  8. customThe residue was chromatographed over silica eluting with 10% methanol in ethyl acetate

Sources & evidence

ORD record
ord-1dfb6fb7964942569b1237c1c3df3738
Source dataset
uspto-grants-1989_07
Patent number
US04851412

Reaction notes

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