Potassium Carbonate → Ethyl 5-(3-aminoquinolin-4-ylamino)pentanoate

HRID 2366680노트

반응식

HRID 2366680 반응식
[N+:1]([C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:13]=1[NH:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:11][CH:10]=[CH:9][CH:8]=2)([O-])=O.S(S([O-])=O)([O-])=O.[Na+].[Na+].C(=O)([O-])[O-].[K+].[K+]>ClCCl.O.CC[N+]1C=CC(C2C=C[N+](CC)=CC=2)=CC=1.[Br-].[Br-].S(S([O-])=O)([O-])=O.[Na+].[Na+]>[NH2:1][C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:13]=1[NH:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:11][CH:10]=[CH:9][CH:8]=2

참가 물질

8

반응물 3

HCID 11430Potassium CarbonateHCID 24489Sodium DithioniteHCID 57447067Ethyl 5-(3-nitroquinolin-4-ylamino)pentanoate

생성물 1

HCID 57447068Ethyl 5-(3-aminoquinolin-4-ylamino)pentanoate수율 96.1%

시약·촉매·용매 4

HCID 24489Sodium Dithionite촉매HCID 114742621,1'-Diethyl-4,4'-bipyridinium dibromide촉매HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

A solution of ethyl 5-(3-nitroquinolin-4-ylamino)pentanoate (151 g, 476 mmol) in dichloromethane (1 L) was added to a solution of sodium hydrosulfite (248.5 g, 1.427 mol), potassium carbonate (259.3 g, 1.876 mol), and ethyl viologen dibromide (1.78 g, 4.75 mmol) in water (1 L), and the reaction was stirred overnight at ambient temperature. An analysis by TLC indicated the presence of starting material; additional sodium hydrosulfite (5.0 g, 29 mmol) was added to the reaction, which was stirred for one additional hour. The organic layer was separated, washed with water (3×), dried over magnesium sulfate, filtered, and concentrated under reduced pressure to provide 131.51 g of ethyl 5-(3-aminoquinolin-4-ylamino)pentanoate.

후처리

  1. stirringwas stirred for one additional hour
  2. customThe organic layer was separated
  3. washwashed with water (3×)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-1c588760b1d44ee7a9d6bd225ab0afeb
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08697873B2

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