Toluene → 2-Amino-4-(2,4-dichloro-phenyl)-5,6-dihydro-benzo[h]quinoline-3-carbonitrile

HRID 392182

반응식

HRID 392182 반응식
[Cl:1][C:2]1[CH:13]=[C:12]([Cl:14])[CH:11]=[CH:10][C:3]=1[CH:4]=[C:5]([C:8]#[N:9])[C:6]#[N:7].[CH2:15]1[CH2:25][C:23](=O)[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:16]1.C([O-])(=O)C.[NH4+:30].C1(C)C=CC=CC=1>C(OCC)(=O)C>[NH2:9][C:8]1[C:5]([C:6]#[N:7])=[C:4]([C:3]2[CH:10]=[CH:11][C:12]([Cl:14])=[CH:13][C:2]=2[Cl:1])[C:25]2[CH2:15][CH2:16][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][C:22]=3[C:23]=2[N:30]=1

참가 물질

6

반응물 4

HCID 1140TolueneHCID 107241-TetraloneHCID 180892,4-DichlorobenzylidenemalononitrileHCID 517165Ammonium Acetate

생성물 1

HCID 226635122-Amino-4-(2,4-dichloro-phenyl)-5,6-dihydro-benzo[h]quinoline-3-carbonitrile수율 47.4%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

A mixture of 2-(2,4-dichloro-benzylidene)-malononitrile (1.125 g, 5 mmol), alpha-tetralone (735 mg, 5 mmol), ammonium acetate (578 mg, 7.5 mmol), and toluene (5 ml) was stirred for 3 h at reflux. Upon cooling to room temperature, the mixture was taken up in ethyl acetate and extracted with satd. NaHCO3, water, and satd. NaCl, and dried over Na2SO4. The solvent was then evaporated and the title compound (868 mg, 47%), MS: m/e=365.9 (M+H+), was isolated from the residue by column chromatography (silica gel, hexanes, ethyl acetate).

후처리

  1. temperatureat reflux
  2. extractionextracted with satd
  3. dry with materialNaCl, and dried over Na2SO4
  4. customThe solvent was then evaporated

출처 및 근거

ORD 기록
ord-db123ef6cc7941fa984100ea1f66978f
출처 데이터셋
uspto-grants-2004_10
특허 번호
US06800650B2

연결된 노트

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