1-Methyl-7-nitro-1,2,3,4-tetrahydroquinoline → 1-Methyl-1,2,3,4-tetrahydroquinolin-7-amine

HRID 494172노트

반응식

HRID 494172 반응식
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([N+:12]([O-])=O)[CH:10]=2)[CH2:5][CH2:4][CH2:3]1>[Pd].CO>[NH2:12][C:9]1[CH:10]=[C:11]2[C:6]([CH2:5][CH2:4][CH2:3][N:2]2[CH3:1])=[CH:7][CH:8]=1

참가 물질

4

반응물 1

HCID 114809551-Methyl-7-nitro-1,2,3,4-tetrahydroquinoline

생성물 1

HCID 112174211-Methyl-1,2,3,4-tetrahydroquinolin-7-amine수율 57%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 887Methanol용매

실험 절차

A mixture of 1-methyl-7-nitro-1,2,3,4-tetrahydroquinoline (D2) (5.35 g, 27.9 mmol) and 10% palladium on charcoal (2 g, 54% water) in methanol (150 ml) was hydrogenated at atmospheric pressure and ambient temperature temperature for 3 d. The catalyst was filtered off and washed with further methanol. The combined filtrated and washings were concentrated in vacuo to give the crude product, which was purified by flash column chromatography. Elution with 5-10% EtOAc/DCM gave the title compound as a brown oil (2.58 g). 1H NMR (250 MHz, CDCl3) δ(ppm): 6.73 (dd, 1H), 5.99 (m, 2H), 3.49 (br, 1H), 3.18 (m, 2H), 2.84 (s, 3H), 2.66 (t, 2H), 1.93 (m, 2H).

후처리

  1. filtrationThe catalyst was filtered off
  2. washwashed with further methanol
  3. filtrationThe combined filtrated
  4. concentrationwashings were concentrated in vacuo
  5. customto give the crude product, which
  6. customwas purified by flash column chromatography
  7. washElution with 5-10% EtOAc/DCM

출처 및 근거

ORD 기록
ord-4e310a0df519445781979b6bdef880cb
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07538121B2

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