6-Benzyl-5-[2-(4-methoxy-phenyl)-ethyl]-5,6-dihydro-[1,6]naphthyridine → 5-[2-(4-Methoxy-phenyl)-ethyl]-5,6,7,8-tetrahydro-[1,6]naphthyridine

HRID 563927노트

반응식

HRID 563927 반응식
C([N:8]1[CH:17]=[CH:16][C:15]2[N:14]=[CH:13][CH:12]=[CH:11][C:10]=2[CH:9]1[CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=1)C1C=CC=CC=1>CO.C(O)(=O)C.[Pd]>[CH3:27][O:26][C:23]1[CH:24]=[CH:25][C:20]([CH2:19][CH2:18][CH:9]2[NH:8][CH2:17][CH2:16][C:15]3[N:14]=[CH:13][CH:12]=[CH:11][C:10]2=3)=[CH:21][CH:22]=1

참가 물질

5

반응물 1

HCID 598200166-Benzyl-5-[2-(4-methoxy-phenyl)-ethyl]-5,6-dihydro-[1,6]naphthyridine

생성물 1

HCID 598199895-[2-(4-Methoxy-phenyl)-ethyl]-5,6,7,8-tetrahydro-[1,6]naphthyridine수율 93.6%

시약·촉매·용매 3

HCID 23938Palladium촉매HCID 176Acetic Acid용매HCID 887Methanol용매

실험 절차

To a solution of 2.1 g (5.85 mmol) 6-benzyl-5-[2-(4-methoxy-phenyl)-ethyl]-5,6-dihydro-[1,6]naphthyridine in 70 mL methanol and 7 mL acetic acid was added 210 mg Pd/C 10% and hydrogenated at atmospheric pressure for 4 h at 55° C. The apparatus was purged with argon, the catalyst was filtered and the filtrate was concentrated in vacuo. The oil was dissolved in ethyl acetate and the solution was washed once with a sat. NaHCO3 solution. The aqueous layer was extracted twice with ethyl acetate and the combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo to yield 1.47 g (93%) of the title compound was yielded as yellow oil.

후처리

  1. customThe apparatus was purged with argon
  2. filtrationthe catalyst was filtered
  3. concentrationthe filtrate was concentrated in vacuo
  4. dissolutionThe oil was dissolved in ethyl acetate
  5. washthe solution was washed once with a sat. NaHCO3 solution
  6. extractionThe aqueous layer was extracted twice with ethyl acetate
  7. dry with materialthe combined organic layers were dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-092e02344dc2446b882ae54982218f08
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08067598B2

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