3-Nitrobenzaldehyde → 3-carboethoxy-2-trifluoromethyl-2-hydroxy-4-(3-nitrophenyl)-4,6,7,8-tetrahydro-5(1H)-quinolone

HRID 2209520

反応式

HRID 2209520 の反応式
[F:1][C:2]([F:12])([F:11])[C:3](=[O:10])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].[C:13]1(=[O:20])[CH2:18][CH2:17][CH2:16][C:15](=O)[CH2:14]1.[N+:21]([C:24]1[CH:25]=[C:26]([CH:29]=[CH:30][CH:31]=1)[CH:27]=O)([O-:23])=[O:22].C([O-])(=O)C.[NH4+:36]>C(O)C>[C:5]([CH:4]1[CH:27]([C:26]2[CH:29]=[CH:30][CH:31]=[C:24]([N+:21]([O-:23])=[O:22])[CH:25]=2)[C:14]2[C:13](=[O:20])[CH2:18][CH2:17][CH2:16][C:15]=2[NH:36][C:3]1([C:2]([F:11])([F:12])[F:1])[OH:10])([O:7][CH2:8][CH3:9])=[O:6]

参加物

6

反応物 4

HCID 74493-NitrobenzaldehydeHCID 104341,3-CyclohexanedioneHCID 67793Ethyl 4,4,4-trifluoroacetoacetateHCID 517165Ammonium Acetate

生成物 1

HCID 199589053-carboethoxy-2-trifluoromethyl-2-hydroxy-4-(3-nitrophenyl)-4,6,7,8-tetrahydro-5(1H)-quinolone

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A stirred mixture of ethyl 4,4,4-trifluoroacetoacetate (6.00 mL), 1,3-cylohexanedione (4.65 g), 3-nitrobenzaldehyde (6.31 g), and ammonium acetate (6.57 g) in ethanol (350 mL) was heated at reflux for 4.5 hours. After removal of solvent the orange residue was treated diethyl ether, and the resulting precipitate was collected by filtration. The solid was triturated with hot diethyl ether, collected, and purified by chromatography (ethyl acetate) to yield 3-carboethoxy-2-trifluoromethyl-2-hydroxy-4-(3-nitrophenyl)-4,6,7,8-tetrahydro-5(1H)-quinolone (8.47 g) as a white solid. NMR: 0.85 (t,3, J=7.1, CH3), 1.86 (m,2, CH2), 2.07 (m,2, CH2), 2.27-2.44 (m,1, CH2), 2.57-2.72 (m,1, CH2), 2.75 (d,1, J=11.9, CH), 3.83 (m,2, CH2), 4.07 (d,1, J=11.4, CH), 7.30 (s,1, OH), 7.50 (m,1, Ar), 7.57 (m,1, Ar), 7.87 (m,1, Ar), 8.01 (m,1, Ar), 8.16 (s,1, NH); MS: m/z=428(M).

後処理

  1. temperaturewas heated
  2. temperatureat reflux for 4.5 hours
  3. customAfter removal of solvent the orange residue
  4. additionwas treated diethyl ether
  5. filtrationthe resulting precipitate was collected by filtration
  6. customThe solid was triturated with hot diethyl ether
  7. customcollected
  8. custompurified by chromatography (ethyl acetate)

出典と根拠

ORDレコード
ord-0c72ab7d2c094e37ab87e0b6f36effa9
出典データセット
uspto-grants-1995_10
特許番号
US05455253

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