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

HRID 1576108노트

반응식

HRID 1576108 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 3283Diethyl Ether용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-ab2e1586e69d487ba25657aed26591cc
출처 데이터셋
uspto-grants-1976_09
특허 번호
US03979410

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