Potassium Carbonate → HCID 68874499, compound

HRID 2366626Notes

Reaction equation

HRID 2366626 reaction equation
[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

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 24489Sodium Dithionite3×HCID 68873567HCID 68873567, compound

Product 1

HCID 68874499HCID 68874499, compoundYield 81.9%

Reagents, catalysts & solvents 1

HCID 114742621,1'-Diethyl-4,4'-bipyridinium dibromideCatalyst

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-d0ddc8e535f34a8383c73adcc9a08e22
Source dataset
uspto-grants-2014_04
Patent number
US08697873B2

Reaction notes

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