Tert-butyl 4-cyanobenzoate → 4-(Amino-hydroxyimino)methylbenzoic acid t-butyl ester

HRID 1417186ノート

反応式

HRID 1417186 の反応式
[C:1]([O:5][C:6](=[O:15])[C:7]1[CH:12]=[CH:11][C:10]([C:13]#[N:14])=[CH:9][CH:8]=1)([CH3:4])([CH3:3])[CH3:2].Cl.[NH2:17][OH:18].C(=O)([O-])O.[Na+]>C(O)(C)(C)C.O>[C:1]([O:5][C:6](=[O:15])[C:7]1[CH:8]=[CH:9][C:10]([CH:13]=[N:14][O:18][NH2:17])=[CH:11][CH:12]=1)([CH3:4])([CH3:2])[CH3:3]

参加物

6

反応物 3

HCID 271408Tert-butyl 4-cyanobenzoateHCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium Bicarbonate

生成物 1

HCID 544161174-(Amino-hydroxyimino)methylbenzoic acid t-butyl ester収率 88.2%

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 6386tert-Butanol溶媒

反応条件

温度
80 °C

実験手順

In a mixture of 21.2 ml of t-butanol and 2.1 ml of water were dissolved 4.3 g of 4-cyanobenzoic t-butyl ester, 1.84 g of hydroxylamine hydrochloride and 2.31 g of sodium hydrogen carbonate. The solution was stirred for 2 hours at 80° C. To the reaction mixture was added water, and the mixture was subjected to extraction with ethyl acetate. The organic layer was concentrated under reduced pressure. The concentrate was purified by means of silica gel column chromatography (hexane/ethyl acetate=1/1), followed by crystallization from hexane to afford 4.41 g of the title compound as colorless needles.

後処理

  1. extractionthe mixture was subjected to extraction with ethyl acetate
  2. concentrationThe organic layer was concentrated under reduced pressure
  3. customThe concentrate was purified by means of silica gel column chromatography (hexane/ethyl acetate=1/1)
  4. customfollowed by crystallization from hexane

出典と根拠

ORDレコード
ord-4a6c9e1932b6473386e78a32bd79f87d
出典データセット
uspto-grants-1999_03
特許番号
US05876756

反応ノート

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