Potassium Carbonate → HCID 68874499, compound

HRID 2366630Notes

Reaction equation

HRID 2366630 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 Dithionite2×HCID 68873567HCID 68873567, compound

Product 1

HCID 68874499HCID 68874499, compound

Reagents, catalysts & solvents 1

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

Procedure

Ethyl N-(3-nitroquinolin-4-yl)-β-alaninate (41.6 g, 144 mmol, prepared as described in Part A of Example 15) was treated with sodium hydrosulfite (87.62 g, 503.3 mmol), potassium carbonate (78.5 g, 568 mmol), and ethyl viologen dibromide (0.54 g, 1.4 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 one additional hour. The organic layer was separated, washed with water (5×200 mL), dried over magnesium sulfate, filtered, and concentrated under reduced pressure to provide 33.3 g of ethyl N-(3-aminoquinolin-4-yl)-β-alaninate.

Workup

  1. stirringthe reaction was stirred for one additional hour
  2. customThe organic layer was separated
  3. washwashed with water (5×200 mL)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0821a5dc4e1448b6b1a9bf8301707a46
Source dataset
uspto-grants-2014_04
Patent number
US08697873B2

Reaction notes

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