Hydrochloric Acid → 6-chloro-5-(3,4-dimethoxyphenyl)-1H-indole-3-carboxylic acid

HRID 338320노트

반응식

HRID 338320 반응식
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]([O:13]C)=[O:12])=[CH:7][NH:8]2)=[CH:4][C:3]=1[C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([O:23][CH3:24])[CH:16]=1.CO.[OH-].[Na+].Cl>C(OCC)(=O)C.C(Cl)Cl>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]([OH:13])=[O:12])=[CH:7][NH:8]2)=[CH:4][C:3]=1[C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([O:23][CH3:24])[CH:16]=1

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 887Methanol2회HCID 14798Sodium HydroxideHCID 86698666methyl 6-chloro-5-(3,4-dimethoxyphenyl)-1H-indole-3-carboxylate

생성물 1

HCID 866986676-chloro-5-(3,4-dimethoxyphenyl)-1H-indole-3-carboxylic acid수율 24%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

A solution of methyl 6-chloro-5-(3,4-dimethoxyphenyl)-1H-indole-3-carboxylate (75 mg, 0.22 mmol), methanol (2.2 mL), and aqueous sodium hydroxide (1M, 0.75 mL, 0.75 mmol) was heated at 75° C. for 24 hours. The reaction was acidified with 1M HCl to pH=2 then diluted with ethyl acetate. The aqueous layer was back-extracted twice with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo to provide a crude solid. The crude product was dissolved in methylene chloride and methanol and silica gel was added. The solvent was removed in vacuo and the crude material adsorbed onto silica was loaded onto a column of silica gel and eluted with ethyl acetate (with 0.2% formic acid)/heptanes (1:1 to 1:0) to provide the title compound (17 mg, 24%) as a tan solid.

후처리

  1. extractionThe aqueous layer was back-extracted twice with ethyl acetate
  2. dry with materialThe combined organic layers were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto provide a crude solid
  6. customThe solvent was removed in vacuo
  7. washeluted with ethyl acetate (with 0.2% formic acid)/heptanes (1:1 to 1:0)

출처 및 근거

ORD 기록
ord-42f33efa79e1451395cc522a2a7331af
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08889730B2

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