Benzylamine → N-benzyl-2-(5-bromopyridin-2-yl)acetamide

HRID 547427Notes

Reaction equation

HRID 547427 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5](=[C:8]2[C:13](=[O:14])OC(C)(C)OC2=O)[NH:6][CH:7]=1.[CH2:18]([NH2:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C1(C)C=CC=CC=1>[CH2:18]([NH:25][C:13](=[O:14])[CH2:8][C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][N:6]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 574434985-(5-Bromopyridin-2(1H)-ylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione

Product 1

HCID 59000711N-benzyl-2-(5-bromopyridin-2-yl)acetamideYield 96.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A flask was charged with 5-(5-bromopyridin-2(1H)-ylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione (1.039 g, 3.46 mmol), benzylamine (0.50 mL, 4.58 mmol), and toluene (20 mL). The reaction was brought to reflux under nitrogen for 18 hours, then cooled and placed in a freezer until cold. The product Was collected by filtration and washed with hexanes to yield a mass of bright white crystals (1.018 g, 96%).

Workup

  1. temperatureto reflux under nitrogen for 18 hours
  2. temperaturecooled
  3. filtrationThe product Was collected by filtration
  4. washwashed with hexanes

Sources & evidence

ORD record
ord-5b8f85c070cd4d9cb86eca0bce1e5d38
Source dataset
uspto-grants-2011_05
Patent number
US07939529B2

Reaction notes

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