7-Nitro-1-trifluoroacetyl-1,2,3,4-tetrahydroquinoline → 1-(7-Amino-3,4-dihydroquinolin-1(2H)-yl)-2,2,2-trifluoroethanone

HRID 494173

반응식

HRID 494173 반응식
[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][CH2:10][N:11]2[C:14](=[O:19])[C:15]([F:18])([F:17])[F:16])=[CH:6][CH:5]=1)([O-])=O>[Pd].CO>[NH2:1][C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][CH2:10][N:11]2[C:14](=[O:19])[C:15]([F:18])([F:16])[F:17])=[CH:6][CH:5]=1

참가 물질

4

반응물 1

HCID 125783617-Nitro-1-trifluoroacetyl-1,2,3,4-tetrahydroquinoline

생성물 1

HCID 820484221-(7-Amino-3,4-dihydroquinolin-1(2H)-yl)-2,2,2-trifluoroethanone수율 96%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 887Methanol용매

실험 절차

A mixture of 7-nitro-1-trifluoroacetyl-1,2,3,4-tetrahydroquinoline (D4) (1.51 g, 5.5 mmol) and 10% palladium on charcoal (150 mg, 54% water) in methanol (80 ml) was hydrogenated at atmospheric pressure and ambient temperature for 24 h. The catalyst was removed by filtration and was washed with further methanol. The combined filtrated and washings were concentrated in vacuo to give the title compound as a pale orange solid (1.29 g). 1H NMR (250 MHz, CDCl3) δ (ppm): 7.05 (br, 1H), 6.95 (d, 1H), 6.54 (dd, 1H), 3.78 (m, 2H), 3.65 (br, 2H), 2.74 (br, 2H), 2.03 (m, 2H).

후처리

  1. customThe catalyst was removed by filtration
  2. washwas washed with further methanol
  3. filtrationThe combined filtrated
  4. concentrationwashings were concentrated in vacuo

출처 및 근거

ORD 기록
ord-3f558095e0f045e4a530bc8a8a7e2b1f
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07538121B2

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