Acetophenone → 2-Phenyl-[1,6]naphthyridine-4-carboxylic acid

HRID 268593ノート

反応式

HRID 268593 の反応式
C([O:3][C:4](=[O:20])[C:5]([C:7]1[CH:8]=[N:9][CH:10]=[CH:11][C:12]=1[NH:13]C(=O)C(C)(C)C)=O)C.[OH-].[K+].[C:23]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)(=O)[CH3:24]>C(O)C.[OH-].[Na+]>[C:26]1([C:23]2[CH:24]=[C:5]([C:4]([OH:20])=[O:3])[C:7]3[C:12](=[CH:11][CH:10]=[N:9][CH:8]=3)[N:13]=2)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

参加物

6

反応物 3

HCID 7410AcetophenoneHCID 14797Potassium HydroxideHCID 10778956Ethyl 4-[(2,2-dimethyl-1-oxopropyl)amino]-α-oxo-3-pyridineacetate

生成物 1

HCID 106821072-Phenyl-[1,6]naphthyridine-4-carboxylic acid

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 14798Sodium Hydroxide溶媒

反応条件

温度
100 °C

実験手順

[4-(2,2-Dimethyl-propionylamino)-pyridin-3-yl]-oxo-acetic acid ethyl ester (532 mg, 1.91 mmol) was taken up in ethanol (1.9 mL) and 4N KOH (1.9 mL, 4 equiv) was added. The solution was refluxed for 2-3 h at 100° C., acetophenone (0.446 mL, 2.0 equiv) was added neat, and the reaction was allowed to reflux overnight. Upon cooling to room temperature, the solution was diluted with 1N NaOH and extracted twice with ether. The product was precipitated from the aqueous layer by the addition of glacial AcOH (5-10 mL). The solids were collected by vacuum filtration, rinsed with cold water, and dried under high vacuum (white solid, 371 mg, 78%). 1H NMR (400 MHz, DMSO-d6) δ 10.00 (s, 1 H), 8.80 (d, J=5.6 Hz, 1 H), 8.56 (s, 1 H), 8.35-8.31 (m, 2 H), 8.03 (d, J=6.0 Hz, 1 H), 7.61-7.58 (m, 3 H). MS (LR-APCI) calcd. for C15H11N2O2 (M+H) 251.1; found 251.5.

後処理

  1. temperatureto reflux overnight
  2. temperatureUpon cooling to room temperature
  3. extractionextracted twice with ether
  4. customThe product was precipitated from the aqueous layer by the addition of glacial AcOH (5-10 mL)
  5. filtrationThe solids were collected by vacuum filtration
  6. washrinsed with cold water
  7. customdried under high vacuum (white solid, 371 mg, 78%)

出典と根拠

ORDレコード
ord-5054df8c00204f88a0d86b3d4f805c73
出典データセット
uspto-grants-2008_11
特許番号
US07446112B2

反応ノート

読み込み中…