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

HRID 2366680ノート

反応式

HRID 2366680 の反応式
[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

参加物

8

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 24489Sodium Dithionite触媒HCID 114742621,1'-Diethyl-4,4'-bipyridinium dibromide触媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-1c588760b1d44ee7a9d6bd225ab0afeb
出典データセット
uspto-grants-2014_04
特許番号
US08697873B2

反応ノート

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