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

HRID 386601Notes

Reaction equation

HRID 386601 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.S(=O)(=O)(O)O.[NH4+].[OH-:18].[CH3:19][C:20]#[N:21]>O>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([NH:21][C:20](=[O:18])[CH3:19])([CH3:10])[CH3:9])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 6342AcetonitrileHCID 14923Ammonium HydroxideHCID 125621182-(6-Chloropyridin-3-yl)propan-2-ol2×

Product 1

HCID 77231171N-(2-(6-chloropyridin-3-yl)propan-2-yl)acetamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of the product from Step A, 1-A, (33.42 g, 195 mmol) in CH3CN (250 mL) was cooled to 0° C. using an ice-water bath. Sulfuric acid (72.7 mL, 1363 mmol) was slowly added and the reaction mixture was allowed to warm to rt and was stirred between 48-72 h. The reaction mixture was cooled to 0° C. using an ice-water bath, diluted with H2O (100 mL) and subsequently treated slowly with aq. 29% NH4OH (203 mL). The quenched mixture was extracted with MTBE and the organic layer was separated. The aqueous layer was extracted with MTBE and the combined organic layers were concentrated under reduced pressure until a solid was present. The solids were treated with hexanes, collected by vacuum filtration and dried under high vacuum. HPLC/MS: 213.0 (M+1); Rt=1.71 min.

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. extractionThe quenched mixture was extracted with MTBE
  3. customthe organic layer was separated
  4. extractionThe aqueous layer was extracted with MTBE
  5. concentrationthe combined organic layers were concentrated under reduced pressure until a solid
  6. additionThe solids were treated with hexanes
  7. filtrationcollected by vacuum filtration
  8. customdried under high vacuum

Sources & evidence

ORD record
ord-111e4bf17de74c88a7f0e23f26ef2b9b
Source dataset
uspto-grants-2013_02
Patent number
US08372857B2

Reaction notes

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