Acetic Acid → 1-Benzyl-7-hydroxy-1,2,3,4-tetrahydro-quinoline-6-carbonitrile

HRID 856960ノート

反応式

HRID 856960 の反応式
[CH2:1]([N:8]1[C:17]2[C:12](=[CH:13][C:14]([CH:19]=O)=[C:15]([OH:18])[CH:16]=2)[CH2:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(=O)C.[N+:25](CC)([O-])=O.C([O-])(=O)C.[Na+]>O>[CH2:1]([N:8]1[C:17]2[C:12](=[CH:13][C:14]([C:19]#[N:25])=[C:15]([OH:18])[CH:16]=2)[CH2:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

6

反応物 4

HCID 176Acetic AcidHCID 6587NitroethaneHCID 517045Sodium AcetateHCID 218649621-Benzyl-7-hydroxy-1,2,3,4-tetrahydro-quinoline-6-carbaldehyde

生成物 1

HCID 218649691-Benzyl-7-hydroxy-1,2,3,4-tetrahydro-quinoline-6-carbonitrile収率 45%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
115 °C

実験手順

To a solution of 1-benzyl-7-hydroxy-1,2,3,4-tetrahydro-quinoline-6-carbaldehyde (45 mg, 0.17 mmol) from step 3 in acetic acid (0.38 mL, 6.6 mmol) was added nitroethane (0.24 mL, 3.4 mmol) and sodium acetate (270 mg, 3.4 mmol). The reaction mixture was heated at a sealed tube at 115° C. overnight. Added some water and extracted it with ether. Combined organic layer and evaporated under vacuum. It was purified by prep TLC eluting with 10% ethyl acetate-hexane and providing 20 mg (45%) of the title compound. 1H-NMR (CDCl3) δ 7.36–7.21 (m, 3H), 7.18–7.14 (m, 2H), 6.99 (s, 1H), 5.98 (s, 1H), 4.48 (s, 2H), 3.41 (t, J=5.7 Hz, 2H), 2.70 (t, J=6.4 Hz, 2H), 1.97 (m, 2H).

後処理

  1. extractionextracted it with ether
  2. customCombined organic layer and evaporated under vacuum
  3. customIt was purified by prep TLC
  4. washeluting with 10% ethyl acetate-hexane

出典と根拠

ORDレコード
ord-45f8f82a8e064ea281f92656f36f41df
出典データセット
uspto-grants-2006_12
特許番号
US07144885B2

反応ノート

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