Nitric Acid → 6-Nitro-2,3-dihydro-1H-indene-1-carboxylic acid

HRID 351755ノート

反応式

HRID 351755 の反応式
[CH:1]1([C:10]([OH:12])=[O:11])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[N+:13]([O-])([OH:15])=[O:14]>ClCCl.OS(O)(=O)=O>[N+:13]([C:7]1[CH:8]=[C:9]2[C:4]([CH2:3][CH2:2][CH:1]2[C:10]([OH:12])=[O:11])=[CH:5][CH:6]=1)([O-:15])=[O:14]

参加物

5

反応物 2

HCID 944Nitric AcidHCID 857281H-Indene-1-carboxylic acid, 2,3-dihydro-

生成物 1

HCID 123184886-Nitro-2,3-dihydro-1H-indene-1-carboxylic acid収率 112.1%

試薬・触媒・溶媒 2

HCID 1118Sulfuric Acid溶媒2 回HCID 6344Dichloromethane溶媒

実験手順

A solution of 1-indancarboxylic acid (30 g), prepared according to the method of Hansen et al. Helv. Chim. Acta 1982, 33, 325-343, in dichloromethane (50 ml) was mixed with concentrated sulphuric acid (300 ml) at −10° C. A mixture of 100% HNO3 (11.4 g) in concentrated H2SO4 (96 ml) was added dropwise under vigorous stirring below −10° C. After stirring for one hour at 10° C., the mixture was poured onto ice. Extraction with ethyl acetate (2×300 ml), drying (anh. MgSO4) and finally evaporation of the organic solvent afforded 42 g of the title compound. Mp: 126-130° C. 5-Nitro-3-benzothiophencarboxylic acid was prepared from 3-bromo-5-nitrobenzothiophene via the corresponding 3-cyanobenzothiophene derivative according to EP Pat. No. 88-301073 (CA110(9):75203y (1988), J. Amer. Chem. Soc. 1948, 70, 1955, and J. Chem. Soc.(c) 1967, 1899.

後処理

  1. additionwas added dropwise
  2. stirringAfter stirring for one hour at 10° C.
  3. additionthe mixture was poured onto ice
  4. extractionExtraction with ethyl acetate (2×300 ml)
  5. customdrying
  6. custom(anh. MgSO4) and finally evaporation of the organic solvent

出典と根拠

ORDレコード
ord-ed26aca75b4e42e790aa3e628323a803
出典データセット
uspto-grants-2004_06
特許番号
US06743808B1

反応ノート

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