Water → 2-[4-(Hydroxymethyl)phenyl]-3-phenyl-1,7-naphthyridin-8(7H)-one

HRID 605007노트

반응식

HRID 605007 반응식
[O-][N+:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:8]([C:12]3[CH:17]=[CH:16][C:15]([CH2:18][OH:19])=[CH:14][CH:13]=3)=[N:9]2)=[CH:4][CH:3]=1.[OH2:26].[OH-].[Na+]>C(OC(=O)C)(=O)C>[OH:19][CH2:18][C:15]1[CH:16]=[CH:17][C:12]([C:8]2[C:7]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:6][C:5]3[CH:4]=[CH:3][NH:2][C:11](=[O:26])[C:10]=3[N:9]=2)=[CH:13][CH:14]=1

참가 물질

5

반응물 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 59846139[4-(7-Oxido-3-phenyl-1,7-naphthyridin-2-yl)phenyl]methanol

생성물 1

HCID 598461492-[4-(Hydroxymethyl)phenyl]-3-phenyl-1,7-naphthyridin-8(7H)-one

시약·촉매·용매 1

HCID 7918Acetic Anhydride용매

반응 조건

온도
130 °C

실험 절차

A suspension of [4-(7-oxido-3-phenyl-1,7-naphthyridin-2-yl)phenyl]methanol (144 mg, 0.44 mmol) in acetic anhydride (2 mL) was heated at 130° C. for two hours and then cooled to ˜100° C. Water was added and the stirred mixture was allowed to cool to room temperature. This solution was extracted with methylene chloride and the organic layer was washed with NaHCO3/Na2CO3 solutions, dried, filtered and the solvent evaporated. This residue was determined to be mainly the acylated product, 4-(7-oxo-3-phenyl-7,8-dihydro-1,7-naphthyridin-2-yl)benzyl acetate, by NMR. This material was dissolved in tetrahydrofuran (5 mL) and 5 N NaOH (0.5 mL, 2.5 mmol) was added. The mixture was heated at 60° C. for two hours. The cooled solution was extracted with methylene chloride. The organic layer was washed with aqueous NaHCO3 and then dried, filtered and the solvent evaporated. The residue was purified by column chromatography on silica gel eluting with 0-5% methanol/ethyl acetate (sat'd with ammonia) to give the title compound. 1H-NMR (500 MHz, CDCl3): δ 10.60 (1H, br s), 7.93 (1H, s), 7.44 (2H, d, J=8 Hz), 7.28-7.34 (4H, m), 7.22-7.27 (4H, m), 6.59 (1H, d, J=7 Hz), 4.65 (2H, s). m/e (m+1): 329.2.

후처리

  1. temperaturecooled to ˜100° C
  2. temperatureto cool to room temperature
  3. extractionThis solution was extracted with methylene chloride
  4. washthe organic layer was washed with NaHCO3/Na2CO3 solutions
  5. customdried
  6. filtrationfiltered
  7. customthe solvent evaporated
  8. dissolutionThis material was dissolved in tetrahydrofuran (5 mL)
  9. temperatureThe mixture was heated at 60° C. for two hours
  10. extractionThe cooled solution was extracted with methylene chloride
  11. washThe organic layer was washed with aqueous NaHCO3
  12. customdried
  13. filtrationfiltered
  14. customthe solvent evaporated
  15. customThe residue was purified by column chromatography on silica gel eluting with 0-5% methanol/ethyl acetate (sat'd with ammonia)

출처 및 근거

ORD 기록
ord-9a5085999e97494dbb04bb94fe78d6a3
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07910561B2

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