Allyl bromide → HCID 57698807、化合物

HRID 552376ノート

反応式

HRID 552376 の反応式
[CH2:1](Br)[CH:2]=[CH2:3].[C:5](ON=O)(C)(C)C.CN[C:14]1[C:15](=[C:19]([N+:23]([O-:25])=[O:24])[CH:20]=[CH:21][CH:22]=1)[C:16]([OH:18])=[O:17]>C(#N)C>[CH2:1]([C:14]1[CH:22]=[CH:21][CH:20]=[C:19]([N+:23]([O-:25])=[O:24])[C:15]=1[C:16]([O:18][CH3:5])=[O:17])[CH:2]=[CH2:3]

参加物

5

反応物 3

HCID 7841Allyl bromideHCID 10906Tert-Butyl nitriteHCID 450893992-(Methylamino)-6-nitrobenzoic acid

生成物 1

HCID 57698807HCID 57698807、化合物収率 62%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

To a stirred solution of allyl bromide (39.7 ml, 459.18 mmol) and tert-butylnitrite (5.5 ml, 45.91 mmol) in acetonitrile (30 ml) was added methyl 6-nitroanthranilic acid (6.0 g, 30.61 mmol) portion-wise at room temperature and the mixture was further stirred for 1 h. The volatile components were evaporated under reduced pressure and the residue was diluted with water. The mixture was extracted with ethyl acetate (2×50 ml) and the combined organic extracts were washed with water and dried over anhydrous sodium sulfate. The residue obtained after evaporation of the solvent was purified by silica gel column chromatography using 5% ethyl acetate in petroleum ether as eluent to give 4.2 g of the product as a yellow oil; 1H NMR (δ ppm, CDCl3, 300 MHz): 7.99 (d, J=7.8, 1H); 7.58-7.46 (m, 2H); 5.93-5.80 (m, 1H), 5.15-5.03 (m, 2H); 3.93 (s, 3H); 3.46 (d, J=6.0, 2H).

後処理

  1. customThe volatile components were evaporated under reduced pressure
  2. additionthe residue was diluted with water
  3. extractionThe mixture was extracted with ethyl acetate (2×50 ml)
  4. washthe combined organic extracts were washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe residue obtained
  7. customafter evaporation of the solvent
  8. customwas purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-b6ceec7506324cc3ac0fc4b013b66174
出典データセット
uspto-grants-2011_05
特許番号
US07951814B2

反応ノート

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