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

HRID 392182

反応式

HRID 392182 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-db123ef6cc7941fa984100ea1f66978f
出典データセット
uspto-grants-2004_10
特許番号
US06800650B2

関連ノート

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