p-Nitroacetophenone → HCID 88069650、化合物

HRID 991557ノート

反応式

HRID 991557 の反応式
[Cl:1][C:2]1[C:7]([C:8]([NH:10][CH2:11][C:12]([OH:14])=[O:13])=O)=[CH:6][CH:5]=[CH:4][N:3]=1.[CH3:15][C:16]([C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=1)=O.C([O-])(=O)C.[Pb+4].C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.C(OC(=O)C)(=O)C>C1COCC1>[Cl:1][C:2]1[C:7]([C:8]2[O:14][C:12](=[O:13])/[C:11](=[C:16](/[C:18]3[CH:19]=[CH:20][C:21]([N+:24]([O-:26])=[O:25])=[CH:22][CH:23]=3)\[CH3:15])/[N:10]=2)=[CH:6][CH:5]=[CH:4][N:3]=1

参加物

6

反応物 4

HCID 7487p-NitroacetophenoneHCID 7918Acetic AnhydrideHCID 53558Glycine, N-(2-chloronicotinoyl)-HCID 178418268HCID 178418268、化合物

生成物 1

HCID 88069650HCID 88069650、化合物収率 20.8%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A mixture of 2-{[(2-chloro-3-pyridinyl)carbonyl]amino}acetic acid (6.44 g, 30 mmol, prepared from glycine and 2-chloronicotinoyl chloride), 4-nitroacetophenone (2.48 g, 15 mmol), lead (IV) acetate (3.33 g, 7.5 mmol) and acetic anhydride in THF (30 ml) was heated at reflux for 4 days. The mixture was poured onto crushed ice, the solid filtered off, washed with water and dried. The brown solid was triturated twice with boiling ethanol and filtered off to give the title compound as a brown solid (1.07 g). δH (CDCl3), 8.57 (1H, dd, J 4.8, 2.1 Hz, PyH), 8.34-8,29 (3H, m, ArH+PyH), 8.05 (2H, d, J 9.1 Hz, ArH), 7.41 (1H, dd, J 7.9, 4.8 Hz, PyH) and 2.84 (3H, s, Me).

後処理

  1. temperaturewas heated
  2. temperatureat reflux for 4 days
  3. additionThe mixture was poured
  4. customonto crushed ice
  5. filtrationthe solid filtered off
  6. washwashed with water
  7. customdried
  8. customThe brown solid was triturated twice with boiling ethanol
  9. filtrationfiltered off

出典と根拠

ORDレコード
ord-4f34db70fe8f424a802c52c2d1c949a8
出典データセット
uspto-grants-2002_10
特許番号
US06465471B1

反応ノート

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