Potassium Carbonate → HCID 68874499、化合物

HRID 2366626ノート

反応式

HRID 2366626 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][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[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+]>CC[N+]1C=CC(C2C=C[N+](CC)=CC=2)=CC=1.[Br-].[Br-]>[NH2:1][C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:13]=1[NH:14][CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:11][CH:10]=[CH:9][CH:8]=2

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 24489Sodium Dithionite3 回HCID 68873567HCID 68873567、化合物

生成物 1

HCID 68874499HCID 68874499、化合物収率 81.9%

試薬・触媒・溶媒 1

HCID 114742621,1'-Diethyl-4,4'-bipyridinium dibromide触媒

実験手順

Ethyl N-(3-nitroquinolin-4-yl)-β-alaninate (28.2 g, 97.5 mmol) was treated with sodium hydrosulfite (50.9 g, 292 mmol), potassium carbonate (53.2 g, 385 mmol), and ethyl viologen dibromide (0.364 g, 0.973 mmol) according to a modification of the method described in Part A of Example 8. After the reaction was stirred overnight, additional sodium hydrosulfite (5.0 g, 29 mmol) was added, and the reaction was stirred for two additional hours. Additional sodium hydrosulfite (2.0 g, 5.3 mmol) was added, and the reaction was stirred for one additional hour. An analysis by TLC indicated the reaction was complete. The organic layer was separated, washed three times with water, and concentrated under reduced pressure to provide 20.7 g of ethyl N-(3-aminoquinolin-4-yl)-β-alaninate.

後処理

  1. stirringthe reaction was stirred for two additional hours
  2. stirringthe reaction was stirred for one additional hour
  3. customThe organic layer was separated
  4. washwashed three times with water
  5. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-d0ddc8e535f34a8383c73adcc9a08e22
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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