Hydrochloric Acid → 4-Chloro-2-methoxycarbonyl-phenyl acetic acid methyl ester

HRID 869423노트

반응식

HRID 869423 반응식
[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[C:8](N)[CH:7]=[CH:6][C:5]=1[CH2:11][C:12]([O:14][CH3:15])=[O:13].N([O-])=O.[Na+].[ClH:21]>Cl[Cu]>[CH3:15][O:14][C:12](=[O:13])[CH2:11][C:5]1[CH:6]=[CH:7][C:8]([Cl:21])=[CH:9][C:4]=1[C:3]([O:2][CH3:1])=[O:16]

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 123467642-Methoxycarbonylmethyl-5-amino-benzoic acid methyl esterHCID 23668193Sodium Nitrite

생성물 1

HCID 128996554-Chloro-2-methoxycarbonyl-phenyl acetic acid methyl ester

시약·촉매·용매 1

HCID 62652Cuprous chloride촉매

실험 절차

5-amino-2-methoxycarbonylmethyl-benzoic acid methyl ester (5 g, 22.4 mmol) was dissolved in hydrochloric acid (50 mL). To the solution was added dropwise aq.NaNO2 (1.7 g, 24.6 mmol) at below 5° C. After addition completed, the color became maroon. Then CuCl (2.4 g, 24.6 mmol) solution was added to the reaction mixture. The reaction mixture was reacted at below 5° C. for 1 hour. The reaction mixture was extracted with dichloromethane. The organic layer was washed with water, dried over anhydrous Na2SO4, concentrated and purified by column chromatography on silica gel (petroleum ether/ethyl acetate=10/1) to give 2.3 g of 5-chloro-2-methoxycarbonylmethyl-benzoic acid methyl ester (18E).

후처리

  1. additionTo the solution was added dropwise aq
  2. customat below 5° C
  3. additionAfter addition
  4. customThe reaction mixture was reacted at below 5° C. for 1 hour
  5. extractionThe reaction mixture was extracted with dichloromethane
  6. washThe organic layer was washed with water
  7. dry with materialdried over anhydrous Na2SO4
  8. concentrationconcentrated
  9. custompurified by column chromatography on silica gel (petroleum ether/ethyl acetate=10/1)

출처 및 근거

ORD 기록
ord-0158c757d10a489da2d1370808269264
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08969373B2

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