Acetic Anhydride → HCID 58268614, compound

HRID 1517562Notes

Reaction equation

HRID 1517562 reaction equation
[Cl:1][C:2]1[C:7]([CH2:8][NH2:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[C:10](OC(=O)C)(=[O:12])[CH3:11].C(N(CC)CC)C>ClCCl>[Cl:1][C:2]1[C:7]([CH2:8][NH:9][C:10](=[O:12])[CH3:11])=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 10898820(2-chloropyridin-3-yl)methanamine

Product 1

HCID 58268614HCID 58268614, compoundYield 47.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2-chloro-3-pyridyl)methanamine (300 mg, 2.10 mmol) in dichloromethane (2 mL) at room temperature is added acetic acid anhydride (198.88 mL, 2.10 mmol) and triethylamine (293.26 mL, 2.10 mmol). After 1 h the reaction is quenched with saturated aqueous solution of sodium bicarbonate and extracted with dichloromethane. The organic layer was separated, dried over magnesium sulfate and the solvent evaporated in vacuo to afford 184 mg of N-[(2-chloro-3-pyridyl)methyl]acetamide. MS (m/z): 185 (M+1)

Workup

  1. customAfter 1 h the reaction is quenched with saturated aqueous solution of sodium bicarbonate
  2. extractionextracted with dichloromethane
  3. customThe organic layer was separated
  4. dry with materialdried over magnesium sulfate
  5. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-c4d0cc96a440433cb4c3b2dba67548cf
Source dataset
uspto-grants-2012_07
Patent number
US08232289B2

Reaction notes

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