Hydrochloric Acid → 4-(5-Methoxy-3-phenyl-1,6-naphthyridin-2-yl)benzaldehyde

HRID 604987노트

반응식

HRID 604987 반응식
[O:1]1CCO[CH:2]1[C:6]1[CH:11]=[CH:10][C:9]([C:12]2[C:21]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:20][C:19]3[C:14](=[CH:15][CH:16]=[N:17][C:18]=3[O:28][CH3:29])[N:13]=2)=[CH:8][CH:7]=1.Cl.C(OCC)(=O)C.C([O-])([O-])=O.[Na+].[Na+]>C1COCC1>[CH3:29][O:28][C:18]1[N:17]=[CH:16][CH:15]=[C:14]2[C:19]=1[CH:20]=[C:21]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:12]([C:9]1[CH:10]=[CH:11][C:6]([CH:2]=[O:1])=[CH:7][CH:8]=1)=[N:13]2

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 592646202-[4-(1,3-Dioxolan-2-yl)phenyl]-5-methoxy-3-phenyl-1,6-naphthyridine

생성물 1

HCID 598461374-(5-Methoxy-3-phenyl-1,6-naphthyridin-2-yl)benzaldehyde

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 2-[4-(1,3-dioxolan-2-yl)phenyl]-5-methoxy-3-phenyl-1,6-naphthyridine (760 mg, 1.98 mmol) in THF (8 mL) was added 1 N HCl (6 mL) and the solution was stirred for three hours. Ethyl acetate was added and the mixture was made basic with aqueous Na2CO3. The organic layer was dried (Na2SO4), filtered and the solvent evaporated. The residue was triturated with diethyl ether to give pure product. The mother liquors were purified by column chromatography on silica gel and elution with 10-30% ethyl acetate/hexane gave additional product. 1H-NMR (500 MHz, CDCl3): δ 10.10 (1H, s), 8.60 (1H, s), 8.26 (1H, d, J=6 Hz), 7.81 (2H, d, J=8.3 Hz), 7.62 (2H, d, J=8.3 Hz), 7.56 (1H, d, J=6.1 Hz), 7.30-7.32 (3H, m), 7.21-7.23 (2H, m), 4.17 (3H, s). m/e (m+1): 341.1.

후처리

  1. dry with materialThe organic layer was dried (Na2SO4)
  2. filtrationfiltered
  3. customthe solvent evaporated
  4. customThe residue was triturated with diethyl ether
  5. customto give pure product
  6. customThe mother liquors were purified by column chromatography on silica gel and elution with 10-30% ethyl acetate/hexane
  7. customgave additional product

출처 및 근거

ORD 기록
ord-2209d1651f3e4e72a39c3b95aaa4406e
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07910561B2

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