Sodium Hydroxide → HCID 70984314、化合物

HRID 339080

反応式

HRID 339080 の反応式
[NH2:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([OH:11])=[O:10])[CH:5]=[CH:6][CH:7]=1.[CH:12](=O)/[CH:13]=[CH:14]/[CH3:15].[OH-].[Na+].[C:19](=O)(O)[O-].[Na+]>Cl.CO.C(OCC)(=O)C.CCOCC>[CH3:12][C:13]1[CH:14]=[CH:15][C:7]2[C:2](=[CH:3][C:4]([CH2:8][C:9]([O:11][CH3:19])=[O:10])=[CH:5][CH:6]=2)[N:1]=1

参加物

9

反応物 4

HCID 14798Sodium HydroxideHCID 447466CrotonaldehydeHCID 516892Sodium BicarbonateHCID 571807(3-Aminophenyl)acetic acid

生成物 1

HCID 70984314HCID 70984314、化合物

試薬・触媒・溶媒 4

HCID 313Hydrochloric Acid溶媒HCID 887Methanol溶媒HCID 3283Diethyl Ether溶媒HCID 8857Ethyl Acetate溶媒

実験手順

2-(3-aminophenyl)acetic acid (11.0 g, 72.8 mmol) was dissolved in 6 N HCl (200 mL) and heated to reflux. (E)-but-2-enal (11.9 mL, 146 mmol) was added dropwise over 10 minutes. The reaction was heated at reflux for 2 hours. After cooling to ambient temperature, the reaction mixture was basified with sodium hydroxide to pH˜12 and ether (100 mL) was added. The aqueous layer was separated, acidified with saturated potassium hydrogen sulfate to pH˜3-4, extracted with 3:1 CHCl3:IPA (3×300 mL), dried (sodium sulfate) and concentrated to give a solid. The solid was dissolved in MeOH (200 mL). The residue was suspended in ethyl acetate (100 mL) and saturated sodium bicarbonate (50 mL). The organic layer was separated, washed with brine, dried (sodium sulfate) and concentrated. The residue obtained was purified by flash chromatography (5:1 DCM:ethyl acetate) to give methyl 2-(2-methylquinolin-7-yl)acetate as a solid.

後処理

  1. temperatureheated to reflux
  2. temperatureThe reaction was heated
  3. temperatureat reflux for 2 hours
  4. additionwas added
  5. customThe aqueous layer was separated
  6. extractionextracted with 3:1 CHCl3
  7. dry with materialIPA (3×300 mL), dried (sodium sulfate)
  8. concentrationconcentrated
  9. customto give a solid
  10. customThe organic layer was separated
  11. washwashed with brine
  12. dry with materialdried (sodium sulfate)
  13. concentrationconcentrated
  14. customThe residue obtained
  15. customwas purified by flash chromatography (5:1 DCM:ethyl acetate)

出典と根拠

ORDレコード
ord-95c1fe54fc5149898c8905051a9bb4e6
出典データセット
uspto-grants-2014_11
特許番号
US08889704B2

関連ノート

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