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

HRID 52660

반응식

HRID 52660 반응식
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]

참가 물질

6

반응물 3

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

생성물 1

HCID 218248512-Amino-5-(4-chlorophenoxy)benzonitrile수율 9.1%

시약·촉매·용매 2

HCID 23925Iron촉매HCID 702Ethanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-14cc633eef844e6188551abd518bf919
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05616718

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