Sulfuric Acid → 1H-Isoindol-3-amine, 5,6-diethoxy-4-fluoro-, sulfate (1:1)

HRID 732249ノート

反応式

HRID 732249 の反応式
[CH2:1]([O:3][C:4]1[C:5]([F:17])=[C:6]([C:15]#[N:16])[C:7](=[CH:10][C:11]=1[O:12][CH2:13][CH3:14])[C:8]#[N:9])[CH3:2].[S:18](=[O:22])(=[O:21])([OH:20])[OH:19].C(N(CC)CC)C>[OH-].[Pd+2].[OH-].[C].COCCOC>[S:18]([OH:22])([OH:21])(=[O:20])=[O:19].[CH2:13]([O:12][C:11]1[CH:10]=[C:7]2[C:6](=[C:5]([F:17])[C:4]=1[O:3][CH2:1][CH3:2])[C:15]([NH2:16])=[N:9][CH2:8]2)[CH3:14]

参加物

6

反応物 3

HCID 1118Sulfuric Acid2 回HCID 8471TriethylamineHCID 229298414,5-Diethoxy-3-fluorophthalonitrile

生成物 1

HCID 115880541H-Isoindol-3-amine, 5,6-diethoxy-4-fluoro-, sulfate (1:1)収率 72%

試薬・触媒・溶媒 2

HCID 178502593HCID 178502593、化合物触媒HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
-23 °C

実験手順

A mixture of 4,5-diethoxy-3-fluorophthalonitrile (2.34 g, 10 mol) prepared in Preparation Example 1, sulfuric acid (0.56 mL, 10 mol), 20% palladium hydroxide-carbon (0.59 g, 50% hydrate) (20% palladium-carbon powder, palladium hydroxide type (hydrate), N.E. Chemical Corporation) and 1,2-dimethoxyethane (23 mL) was stirred at −23° C. under hydrogen atmosphere (atmospheric pressure) for 29 hours. After insoluble matter in the reaction mixture was filtered off, the residue was washed with methanol (23 mL), and the combined filtrate was divided into five equal portions. To one of them, triethylamine (0.14 mL, 1 mol) was added, and the mixture was stirred at 60° C. for three hours and concentrated at 40° C. under reduced pressure. Methanol (2.3 mL) and 1,2-dimethoxyethane (6.9 mL) were added to the residue, then sulfuric acid (0.11 mL, 2 mol) was added on ice, and the mixture was stirred. Precipitated crystals were filtered, washed with a 5% methanol-1,2-dimethoxyethane solution, and dried at room temperature under reduced pressure to give 0.45 g of the title compound (yield: 72%) as grayish white crystals.

後処理

  1. filtrationAfter insoluble matter in the reaction mixture was filtered off
  2. washthe residue was washed with methanol (23 mL)
  3. stirringthe mixture was stirred at 60° C. for three hours
  4. concentrationconcentrated at 40° C. under reduced pressure
  5. additionMethanol (2.3 mL) and 1,2-dimethoxyethane (6.9 mL) were added to the residue
  6. stirringthe mixture was stirred
  7. customPrecipitated crystals
  8. filtrationwere filtered
  9. washwashed with a 5% methanol-1,2-dimethoxyethane solution
  10. customdried at room temperature under reduced pressure

出典と根拠

ORDレコード
ord-71d5a13e2cff468781edfaff52249ccd
出典データセット
uspto-grants-2009_09
特許番号
US07585982B2

反応ノート

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