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

HRID 10341

反応式

HRID 10341 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 23939Platinum触媒HCID 176Acetic Acid溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-cf7993e3573e421a894de7cb83cffe3e
出典データセット
uspto-grants-2006_08
特許番号
US07094780B1

関連ノート

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