Hexane → 3-Dimethylamino-1-(2-chloro4-pyridyl)-2-propen-1-one

HRID 859102Notes

Reaction equation

HRID 859102 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][N:7]=[C:6]([Cl:10])[CH:5]=1)(=[O:3])[CH3:2].CCCCCC.C(O[CH:20](OCC)[N:21]([CH3:23])[CH3:22])C>>[CH3:20][N:21]([CH3:23])[CH:22]=[CH:2][C:1]([C:4]1[CH:9]=[CH:8][N:7]=[C:6]([Cl:10])[CH:5]=1)=[O:3]

Participants

4

Reactant 3

HCID 8058HexaneHCID 70913Dimethylformamide diethylacetalHCID 131452551-(2-Chloropyridin-4-yl)ethan-1-one

Product 1

HCID 544350393-Dimethylamino-1-(2-chloro4-pyridyl)-2-propen-1-one

Procedure

A mixture of 4-acetyl-2-chloro-pyridine (1.72 g, 11 mmol) in N,N-dimethyl formamide diethyl acetal (10 mL) is heated to reflux for 1 hour and cooled to room temperature before adding hexane (8 mL). The solid is collected by filtration, washed with hexane and dried to give 3-dimethylamino-1-(2-chloro-4-pyridyl)-2-propen-1-one (1.70 g); ESI-MS (m/z): 211.0 (M++H).

Workup

  1. temperatureis heated
  2. temperatureto reflux for 1 hour
  3. filtrationThe solid is collected by filtration
  4. washwashed with hexane
  5. customdried

Sources & evidence

ORD record
ord-7aaa9b482f0e4f958d6bc3762c11f9c4
Source dataset
uspto-grants-2006_12
Patent number
US07151096B2

Reaction notes

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