Water → HCID 68874499, compound

HRID 2366673Notes

Reaction equation

HRID 2366673 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+].O>CC[N+]1C=CC(C2C=C[N+](CC)=CC=2)=CC=1.[Br-].[Br-].ClCCl>[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

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 24489Sodium Dithionite2×HCID 68873567HCID 68873567, compound

Product 1

HCID 68874499HCID 68874499, compound

Reagents, catalysts & solvents 2

HCID 114742621,1'-Diethyl-4,4'-bipyridinium dibromideCatalystHCID 6344DichloromethaneSolvent

Procedure

Ethyl N-(3-nitroquinolin-4-yl)-β-alaninate (62.0 g, 214 mmol, prepared as described in Part A of Example 22) was treated with sodium hydrosulfite (130.59 g, 750.04 mmol), potassium carbonate (117 g, 847 mmol), and ethyl viologen dibromide (0.802 g, 2.14 mmol) according to a modification of the method described in Part A of Example 8. After the reaction was stirred overnight, additional water (100 mL), dichloromethane (100 mL) and sodium hydrosulfite (20.0 g, 11.5 mmol) were added, and the reaction was stirred for three additional hours. The organic layer was separated; washed sequentially with water, saturated aqueous sodium bicarbonate, and brine; dried over magnesium sulfate; filtered; and concentrated under reduced pressure to provide 40.2 g of ethyl N-(3-aminoquinolin-4-yl)-β-alaninate.

Workup

  1. stirringthe reaction was stirred for three additional hours
  2. customThe organic layer was separated
  3. washwashed sequentially with water, saturated aqueous sodium bicarbonate, and brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationand concentrated under reduced pressure

Sources & evidence

ORD record
ord-efb7d07a60cc469f93fc7a8e0992347e
Source dataset
uspto-grants-2014_04
Patent number
US08697873B2

Reaction notes

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