Hydrochloric Acid → HCID 59395032、化合物

HRID 1805166ノート

反応式

HRID 1805166 の反応式
[N+:1]([C:4]1[CH:9]=[C:8]([N+:10]([O-])=O)[CH:7]=[CH:6][C:5]=1[C:13]([OH:22])([C:18]([F:21])([F:20])[F:19])[C:14](OC)=[O:15])([O-])=O.Cl>C(OCC)(=O)C.[Pd]>[NH2:10][C:8]1[CH:9]=[C:4]2[C:5]([C:13]([OH:22])([C:18]([F:21])([F:20])[F:19])[C:14](=[O:15])[NH:1]2)=[CH:6][CH:7]=1

参加物

5

反応物 2

HCID 313Hydrochloric AcidHCID 86643090Methyl α-hydroxy-2,4-dinitro-α-(trifluoromethyl)benzeneacetate

生成物 1

HCID 59395032HCID 59395032、化合物収率 99%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 8857Ethyl Acetate溶媒2 回

実験手順

To a solution of methyl 2-(2,4-dinitrophenyl)-3,3,3-trifluoro-2-hydroxypropanoate (1.3 g, 4.01 mmol) in ethyl acetate (18 mL) was added (pH3) HCl (5.2 mL) followed by 10% Pd/C (350 mg) in ethyl acetate (3 mL). The reaction mixture was stirred overnight under an atmosphere of H2. The reaction mixture was filtered through a pad of Celite and the filtrate was concentrated in vacuo. The crude residue obtained was partitioned between dichloromethane (25 mL) and aqueous saturated NaHCO3 (15 mL). The organic phase was separated and the aqueous phase was extracted dichloromethane (2×25 mL). The combined organic phase was dried over Na2SO4, filtered, and concentrated. The residue was purified by silica gel column chromatography (50-100% ethyl acetate/hexanes) to give 6-amino-3-hydroxy-3-(trifluoromethyl)indolin-2-one (921 mg, 99%)

後処理

  1. filtrationThe reaction mixture was filtered through a pad of Celite
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe crude residue obtained
  4. customwas partitioned between dichloromethane (25 mL) and aqueous saturated NaHCO3 (15 mL)
  5. customThe organic phase was separated
  6. extractionthe aqueous phase was extracted dichloromethane (2×25 mL)
  7. dry with materialThe combined organic phase was dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe residue was purified by silica gel column chromatography (50-100% ethyl acetate/hexanes)

出典と根拠

ORDレコード
ord-a4fef9dac4fd4760bfc772013674e77f
出典データセット
uspto-grants-2013_01
特許番号
US08354427B2

反応ノート

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