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

HRID 268593노트

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HRID 268593 반응식
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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 702Ethanol용매HCID 14798Sodium Hydroxide용매

반응 조건

온도
100 °C

실험 절차

[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.

후처리

  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%)

출처 및 근거

ORD 기록
ord-5054df8c00204f88a0d86b3d4f805c73
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07446112B2

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