Sulfuric Acid → N-(2-(6-chloropyridin-3-yl)propan-2-yl)acetamide

HRID 1525317Notes

Reaction equation

HRID 1525317 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8](O)([CH3:10])[CH3:9])=[CH:4][CH:3]=1.[OH:12]S(O)(=O)=O.[CH3:17][C:18]#[N:19]>[NH4+].[OH-]>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([NH:19][C:18](=[O:12])[CH3:17])([CH3:10])[CH3:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 6342AcetonitrileHCID 125621182-(6-Chloropyridin-3-yl)propan-2-ol2×

Product 1

HCID 77231171N-(2-(6-chloropyridin-3-yl)propan-2-yl)acetamideYield 72.6%

Reagents, catalysts & solvents 1

HCID 14923Ammonium HydroxideSolvent

Procedure

To a solution of 2-(6-chloropyridin-3-yl)propan-2-ol, 33-b, (10 g, 58.3 mmol) in MeCN (100 ml) was added dropwise H2SO4 (40 g, 408 mmol) at 0° C., while keeping the internal temperature below 15° C. After the addition was completed, the reaction mixture was warmed to room temperature and stirred for 24 hours. The reaction mixture was then cooled to 0° C. and diluted with NH4OH slowly. The reaction mixture was then extracted with ether (3×100 mL), dried, and concentrated. The product was purified by silica gel (DCM-DCM:MeOH=30:1) to give a white solid, 33-c, (9 g, 72.6%)

Workup

  1. customthe internal temperature below 15° C
  2. additionAfter the addition
  3. temperatureThe reaction mixture was then cooled to 0° C.
  4. extractionThe reaction mixture was then extracted with ether (3×100 mL)
  5. customdried
  6. concentrationconcentrated
  7. customThe product was purified by silica gel (DCM-DCM:MeOH=30:1)

Sources & evidence

ORD record
ord-d8cd356ece584de38fd937bf06e5fb0a
Source dataset
uspto-grants-2015_07
Patent number
US09079930B2

Reaction notes

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