Acetic Anhydride → N-(4-Bromopyridin-2-yl)acetamide

HRID 537022Notes

Reaction equation

HRID 537022 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH2:8])[CH:3]=1.[NH4+].[OH-].[C:11](OC(=O)C)(=[O:13])[CH3:12]>CN(C1C=CN=CC=1)C>[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH:8][C:11](=[O:13])[CH3:12])[CH:3]=1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 14923Ammonium HydroxideHCID 6932822-Amino-4-bromopyridine

Product 1

HCID 59529635N-(4-Bromopyridin-2-yl)acetamide

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Conditions

Temperature
140 °C

Procedure

To a solution of 4-bromopyridin-2-amine (12.0 g, 69.4 mmol) in acetic anhydride (240 mL) was added DMAP (0.0847 g, 0.694 mmol). The reaction mixture was allowed to stir at 140° C. for 3 h and then allowed to cool to rt. Ice water was added and the pH of the mixture was adjusted to 8.5 by the addition of concentrated NH4OH. The solid which precipitated was filtered, washed with cold water and hexanes, and dried to give N-(4-bromopyridin-2-yl)acetamide (13.3 g) as a white solid.

Workup

  1. temperatureto cool to rt
  2. customThe solid which precipitated
  3. filtrationwas filtered
  4. washwashed with cold water and hexanes
  5. customdried

Sources & evidence

ORD record
ord-f8fdd3093cae4c86945ff34f2937d4ff
Source dataset
uspto-grants-2014_10
Patent number
US08859768B2

Reaction notes

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