Pyridine → 4-(Dimethylamino)-3-(2-nitrophenyl)but-3-en-2-one

HRID 1576108Notes

Reaction equation

HRID 1576108 reaction equation
[CH3:1][N:2]([CH3:14])[CH:3]=[CH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N+:11]([O-:13])=[O:12].N1C=CC=CC=1.[C:21](Cl)(=[O:23])[CH3:22]>CCOCC>[C:21]([C:4]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N+:11]([O-:13])=[O:12])=[CH:3][N:2]([CH3:1])[CH3:14])(=[O:23])[CH3:22]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 54442712N,N-Dimethyl-2-(2-nitrophenyl)ethen-1-amine

Product 1

HCID 541295954-(Dimethylamino)-3-(2-nitrophenyl)but-3-en-2-one

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a stirred solution of 3.84 g. of β-dimethylamino-2-nitrostyrene and 1.61 ml. of pyridine in 20 ml. of ether, was added dropwise a solution of 1.42 ml. of acetyl chloride in 5 ml. of ether. The mixture was stirred for 3 hours at 0° and filtered. The gummy solid was partitioned between methylene chloride and water. The organic phase was washed with dilute hydrochloride, dried and concentrated to a dark oil. The nmr spectrum was in agreement with the proposed structure. This product, i.e., α-acetyl-β-dimethylamino-2-nitrostyrene was used without further purification in the next step.

Workup

  1. filtrationfiltered
  2. customThe gummy solid was partitioned between methylene chloride and water
  3. washThe organic phase was washed with dilute hydrochloride
  4. customdried
  5. concentrationconcentrated to a dark oil
  6. customThis product, i.e., α-acetyl-β-dimethylamino-2-nitrostyrene was used without further purification in the next step

Sources & evidence

ORD record
ord-ab2e1586e69d487ba25657aed26591cc
Source dataset
uspto-grants-1976_09
Patent number
US03979410

Reaction notes

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