Methyl quinoline-5-carboxylate → Methyl 5,6,7,8-tetrahydroquinoline-5-carboxylate

HRID 2173369노트

반응식

HRID 2173369 반응식
[N:1]1[C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([C:11]([O:13][CH3:14])=[O:12])[C:5]=2[CH:4]=[CH:3][CH:2]=1>C(O)(C(F)(F)F)=O.[Pt]=O>[N:1]1[C:10]2[CH2:9][CH2:8][CH2:7][CH:6]([C:11]([O:13][CH3:14])=[O:12])[C:5]=2[CH:4]=[CH:3][CH:2]=1

참가 물질

4

반응물 1

HCID 12503486Methyl quinoline-5-carboxylate

생성물 1

HCID 77230270Methyl 5,6,7,8-tetrahydroquinoline-5-carboxylate

시약·촉매·용매 2

HCID 82844Platinum oxide (PtO)촉매HCID 6422Trifluoroacetic acid용매

실험 절차

Methyl quinoline-5-carboxylate (3.67 g, 19.61 mmol) was dissolved in TFA (60 ml) and added platinum oxide (0.49 g, 2.16 mmol) then hydrogenated at room temperature overnight. Filtered off the catalyst and evaporated to dryness. The residue was chromatographed through a 120 g ISCO Redi-sep column and eluted with 5% of (10% NH4OH in MeOH) in DCM to yield methyl 5,6,7,8-tetrahydroquinoline-5-carboxylate 1H-NMR (600 MHz, CDCl3): δ ppm 8.42 (d, J=3.7 Hz, 1H), 7.485 (d, J=7.7 Hz, 1H), 7.06-7.08 (m, 1H), 3.82 (t, J=5.6 Hz, 1H), 3.72 (d, J=3.2 Hz, 3H), 3.02-2.93 (m, 1H), 2.88-2.93 (m, 1H), 2.16-2.20 (m, 1H), 1.97-2.05 (m, 2H), 1.85-1.90 (m, 1H); LC-MS: M+1=192.

후처리

  1. filtrationFiltered off the catalyst
  2. customevaporated to dryness
  3. customThe residue was chromatographed through a 120 g ISCO Redi-sep column
  4. washeluted with 5% of (10% NH4OH in MeOH) in DCM

출처 및 근거

ORD 기록
ord-a4fe317fdaa545aaa5520b558deab614
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09056859B2

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