Hydrochloric Acid → 2-Amino-5-(4-chlorophenoxy)benzonitrile

HRID 1734622

反応式

HRID 1734622 の反応式
Cl.O.[N+:3]([C:6]1[CH:13]=[CH:12][C:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)=[CH:10][C:7]=1[C:8]#[N:9])([O-])=O>C(O)C.[Fe]>[NH2:3][C:6]1[CH:13]=[CH:12][C:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)=[CH:10][C:7]=1[C:8]#[N:9]

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 218248742-Nitro-5-(4-chlorophenoxy)benzonitrile

生成物 1

HCID 218248512-Amino-5-(4-chlorophenoxy)benzonitrile収率 9.1%

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 702Ethanol溶媒

実験手順

A mixture of 2.0 grams (0.035 mole) of iron powder, 1.0 mL of concentrated hydrochloric acid, 4.0 mL of water, in 30 mL of ethanol was stirred, and 2.5 grams (0.009 mole) of 2-nitro-5-(4-chlorophenoxy)benzonitrile was added slowly. Upon completion of addition, the reacton mixture was warmed to reflux where it stirred for about seven hours. After this time, the reaction mixture was allowed to cool to ambient temperature where it stirred for about 18 hours. The reaction mixture was then warmed and filtered through a pad of diatomaceous earth. The filtrate was concentrated under reduced pressure to a residue. The residue was purified with column chromatography on silica gel, using 1:1 petroleum ether/methylene chloride. The product-containing fractions were combined and concentrated under reduced pressure, yielding 0.2 gram of 2-amino-5-(4-chlorophenoxy)benzonitrile, mp 116°-118° C. The NMR spectrum was consistent with the proposed structure. The reaction was repeated.

後処理

  1. additionUpon completion of addition
  2. temperaturethe reacton mixture was warmed
  3. temperatureto reflux where it
  4. stirringstirred for about 18 hours
  5. temperatureThe reaction mixture was then warmed
  6. filtrationfiltered through a pad of diatomaceous earth
  7. concentrationThe filtrate was concentrated under reduced pressure to a residue
  8. customThe residue was purified with column chromatography on silica gel
  9. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-04f05cdf149040049b50fc2fb88abf13
出典データセット
uspto-grants-1996_07
特許番号
US05534518

関連ノート

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