Hydrochloric Acid → Ethyl 2-(3-chloro-4-fluoro-phenylhydrazino)propionate

HRID 544921

반응식

HRID 544921 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[F:9])[NH2:5].Cl.[N:11]([O-])=O.[Na+].[CH3:15][CH:16](C(C)=O)[C:17]([O:19][CH2:20][CH3:21])=[O:18].[OH-].[K+].C([O-])(=O)C.[Na+]>O.C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([NH:5][NH:11][CH:16]([CH3:15])[C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:6]=[CH:7][C:8]=1[F:9]

참가 물질

9

반응물 6

HCID 313Hydrochloric AcidHCID 701Ethyl 2-methylacetoacetateHCID 97083-Chloro-4-fluoroanilineHCID 14797Potassium HydroxideHCID 517045Sodium AcetateHCID 23668193Sodium Nitrite

생성물 1

HCID 67197345Ethyl 2-(3-chloro-4-fluoro-phenylhydrazino)propionate수율 34.4%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매2회

반응 조건

온도
0 °C

실험 절차

A mixture of 3-chloro-4-fluoroaniline (10.0 g) in a 6 N aqueous hydrochloric acid solution (35 ml) was cooled to 0° C., and thereto was added dropwise a solution of sodium nitrite (4.80 g) in H2O (6.3 ml). After being stirred at same temperature for 25 minutes, the mixture was added to a solution of ethyl 2-methylacetoacetate (11.0 g), potassium hydroxide (21.2 g) and sodium acetate (21.2 g) in ethyl alcohol (80 ml)-H2O (100 ml) in one portion at 0° C. The resultant mixture was stirred at same temperature for 2 hours, and extracted with diethyl ether. The organic layer was washed with water twice and brine followed by being dried over sodium sulfate. The insoluble materials were filtered off, and the filtrate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1-3:1) to give ethyl 2-(3-chloro-4-fluoro-phenylhydrazino)propionate (6.16 g) as a reddish solid. APCI-Mass m/Z 259/261 (M+H).

후처리

  1. extractionextracted with diethyl ether
  2. washThe organic layer was washed with water twice
  3. dry with materialby being dried over sodium sulfate
  4. filtrationThe insoluble materials were filtered off
  5. customthe filtrate was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1-3:1)

출처 및 근거

ORD 기록
ord-0a179adff3f141c2962997c3878a5082
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07935674B2

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