Hydrochloric Acid → N-(3-hydroxy-4-oxo-2-phenyl-chromen-6-yl)acetamide

HRID 250785ノート

反応式

HRID 250785 の反応式
[OH:1]O.[C:3]([NH:6][C:7]1[CH:8]=[CH:9][C:10]([OH:23])=[C:11]([CH:22]=1)[C:12](=[O:21])[CH:13]=[CH:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)(=[O:5])[CH3:4].[OH-].[Na+].Cl>C(O)C>[C:3]([NH:6][C:7]1[CH:22]=[C:11]2[C:10](=[CH:9][CH:8]=1)[O:23][C:14]([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)=[C:13]([OH:1])[C:12]2=[O:21])(=[O:5])[CH3:4]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 91187N-[4-Hydroxy-3-(3-phenylprop-2-enoyl)phenyl]ethanimidic acid

生成物 1

HCID 49864161N-(3-hydroxy-4-oxo-2-phenyl-chromen-6-yl)acetamide収率 50%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

Aqueous hydrogen peroxide (30% w/v, 4 mL) was added to an ice-cold suspension of 5′-acetamido-2′-hydroxychalcone (5) (2.00 g, 7.11 mmol) and 1 M NaOH (20 mL) in ethanol (60 mL). The mixture was allowed to warm to room temperature and was vigorously stirred overnight. The mixture was acidified with 1 M HCl and the precipitate formed was collected by filtration to afford the flavonol (6) as a bright yellow powder (1.04 g, 50%), m.p. 241-242° C. 1H NMR (399.7 MHz, d6-DMSO) δ 2.10 (s, 3H, CH3); 7.48-7.59 (m, 3H, H3′,4′,5′); 7.73 (d, 1H, J7,8 9.2 Hz, H8); 7.89 (dd, 1H, J5,7 2.8, J7,8 9.2 Hz, H7); 8.21 (app. d, 2H, J=7.6 Hz, H2′,6′); 8.44 (d, 1H, J5,7 2.8 Hz, H5), 9.60 (br s, 1H, OH); 10.28 (s, 1H, NH).

後処理

  1. customthe precipitate formed
  2. filtrationwas collected by filtration

出典と根拠

ORDレコード
ord-dd8c8c45ad6145258cd839506aed5489
出典データセット
uspto-grants-2011_01
特許番号
US07863323B1

反応ノート

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