Acetic Anhydride → N-(1-(4-bromopyridin-2-yl)ethyl)acetamide

HRID 879583Notes

Reaction equation

HRID 879583 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH:8]([NH2:10])[CH3:9])[CH:3]=1.[C:11](OC(=O)C)(=[O:13])[CH3:12]>C(Cl)(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH:8]([NH:10][C:11](=[O:13])[CH3:12])[CH3:9])[CH:3]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 826584741-(4-Bromopyridin-2-yl)ethanamine

Product 1

HCID 86700400N-(1-(4-bromopyridin-2-yl)ethyl)acetamide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 1-(4-bromopyridin-2-yl)ethanamine (2.3 g, 11.44 mmol) in chloroform (30 mL) was added acetic anhydride (2.16 mL, 22.88 mmol) dropwise at 0° C. The reaction was then quenched with ice water (40 mL) and extracted with chloroform (2×50 mL). The organic extracts were combined, then washed with 1M NaOH (50 mL), dried over Na2SO4, concentrated, and purified by column chromatography (gradient 0 to 5% MeOH/DCM) to afford the product. 1H NMR (400 MHz, CDCl3) δ 8.35 (d, J=5.3 Hz, 1H), 7.42 (s, 1H), 7.36 (dd, J=5.3, 1.7 Hz, 1H), 6.71 (br s, 1H), 5.10 (p, J=7.0 Hz, 1H), 2.02 (s, 3H), 1.45 (d, J=6.8 Hz, 3H).

Workup

  1. customThe reaction was then quenched with ice water (40 mL)
  2. extractionextracted with chloroform (2×50 mL)
  3. washwashed with 1M NaOH (50 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. custompurified by column chromatography (gradient 0 to 5% MeOH/DCM)
  7. customto afford the product

Sources & evidence

ORD record
ord-5db0260a003344fe9ae23a9866602460
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

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