Pyrrolidine → HCID 136463775、化合物

HRID 862102ノート

反応式

HRID 862102 の反応式
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:21])=[C:6]([CH:20]=1)[C:7]([C:9]1[C:14]([CH:15]2[O:19][CH2:18][CH2:17][O:16]2)=[CH:13][CH:12]=[CH:11][N:10]=1)=O.Cl.[C:23]([O:27][NH2:28])([CH3:26])([CH3:25])[CH3:24].N1CCCC1>C(O)CC>[C:23]([O:27]/[N:28]=[C:7](\[C:9]1[C:14]([CH:15]2[O:19][CH2:18][CH2:17][O:16]2)=[CH:13][CH:12]=[CH:11][N:10]=1)/[C:6]1[CH:20]=[C:2]([Br:1])[CH:3]=[CH:4][C:5]=1[OH:21])([CH3:26])([CH3:25])[CH3:24]

参加物

5

反応物 3

HCID 31268PyrrolidineHCID 2777906O-tert-butylhydroxylamine hydrochlorideHCID 197016352-(5-Bromo-2-hydroxybenzoyl)-3-(1,3-dioxolan-2-yl)pyridine

生成物 1

HCID 136463775HCID 136463775、化合物収率 80%

試薬・触媒・溶媒 1

HCID 10311-Propanol溶媒

実験手順

A solution of 2-(5-bromo-2-hydroxybenzoyl)-3-(1,3-dioxolan-2-yl)pyridine (2.92 g), O-t-butyl-hydroxylamine hydrochloride (2.09 g) and pyrrolidine (1.78 g) in n-propanol (40 ml) was heated for 2 hours under reflux. The reaction mixture was concentrated, to which was added water, followed by subjecting the mixture to extraction with ethyl acetate. The extract solution was washed with a saturated aqueous saline solution, dried (anhydrous sodium sulfate), and concentrated. The concentrate was purified by means of a silica gel column chromatography (eluent: ethyl acetate/hexane) to give (Z)-2-(5-bromo-2-hydroxybenzoyl)-3-(1,3-dioxolan-2-yl)pyridine O-t-butyloxime (2.81 g) (Compound 134).

後処理

  1. temperatureunder reflux
  2. concentrationThe reaction mixture was concentrated, to which
  3. additionwas added water
  4. extractionto extraction with ethyl acetate
  5. washThe extract solution was washed with a saturated aqueous saline solution
  6. dry with materialdried (anhydrous sodium sulfate)
  7. concentrationconcentrated
  8. customThe concentrate was purified by means of a silica gel column chromatography (eluent: ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-a0acd65784ad4ce680a9cb519443478b
出典データセット
uspto-grants-1998_02
特許番号
US05716971

反応ノート

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