Water → 5,6-Difluoro-2-methyl-1,2,3,4-tetrahydro-quinoline-8-carboxylic acid methyl ester

HRID 10341

반응식

HRID 10341 반응식
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([F:17])[C:8]([F:16])=[C:9]2[C:14]=1[N:13]=[C:12]([CH3:15])[CH:11]=[CH:10]2)=[O:4].O.[H][H]>C(O)(=O)C.[Pt]>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([F:17])[C:8]([F:16])=[C:9]2[C:14]=1[NH:13][CH:12]([CH3:15])[CH2:11][CH2:10]2)=[O:4]

참가 물질

6

반응물 3

HCID 962WaterHCID 210411915,6-Difluoro-2-methylquinoline-8-carboxylic acid methyl esterHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 210411905,6-Difluoro-2-methyl-1,2,3,4-tetrahydro-quinoline-8-carboxylic acid methyl ester수율 68.9%

시약·촉매·용매 2

HCID 23939Platinum촉매HCID 176Acetic Acid용매

실험 절차

A solution of 8.0 g (33.7 mmol) of 5,6-difluoro-2-methylquinoline-8-carboxylic acid methyl ester (Example 33) in 100 mL of glacial acetic acid is treated with 2.15 g of platinum on carbon (0.8 g of active catalyst+62.8% water) and then shaken in a hydrogen atmosphere at temperatures of 24° C. to 29° C. and pressures of 23.9 to 46.6 psi for 3 hours. The catalyst is removed by filtration and the solvent is removed in vacuo at 50° C. The residue is triturated with water (50 mL) and extracted with dichloromethane (2×200 mL). The combined organic layers are stirred with 5% sodium bicarbonate solution, washed with water, dried (MgSO4), filtered and evaporated in vacuo. The residue is chromatographed over flash grade silica gel (230–400 mesh) eluting with dichloromethane to give 5.6 g of the title compound as a light yellow oil. 1H NMR (400 MHz, CDCl3): 7.66 (bs, 1H), 7.49 (m, 1H), 3.82 (s, 3H), 3.46 (m, 1H), 2.88 (m, 1H), 2.67 (m, 1H), 1.97 (m, 1H), 1.27 (d, 3H).

후처리

  1. customThe catalyst is removed by filtration
  2. customthe solvent is removed in vacuo at 50° C
  3. customThe residue is triturated with water (50 mL)
  4. extractionextracted with dichloromethane (2×200 mL)
  5. washwashed with water
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customevaporated in vacuo
  9. customThe residue is chromatographed over flash grade silica gel (230–400 mesh)
  10. washeluting with dichloromethane

출처 및 근거

ORD 기록
ord-cf7993e3573e421a894de7cb83cffe3e
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07094780B1

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