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

HRID 1576108ノート

反応式

HRID 1576108 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-ab2e1586e69d487ba25657aed26591cc
出典データセット
uspto-grants-1976_09
特許番号
US03979410

反応ノート

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