Potassium Carbonate → HCID 57447017, compound

HRID 2366619Notes

Reaction equation

HRID 2366619 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][CH2:17][CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])=[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][CH2:17][CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:11][CH:10]=[CH:9][CH:8]=2

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 24489Sodium Dithionite2×HCID 57447021HCID 57447021, compound

Product 1

HCID 57447017HCID 57447017, compoundYield 97.4%

Reagents, catalysts & solvents 1

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

Procedure

Ethyl 6-(3-nitroquinolin-4-ylamino)hexanoate (27.1 g, 81.8 mmol, prepared as described in Parts A and B of Example 6) was treated with sodium hydrosulfite (49.8 g, 286 mmol), potassium carbonate (44.6 g, 323 mmol), and ethyl viologen dibromide (0.306 g, 0.818 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 three times with water, and concentrated under reduced pressure to provide 24 g of ethyl 6-(3-aminoquinolin-4-ylamino)hexanoate.

Workup

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

Sources & evidence

ORD record
ord-e4d1080b4b48432e871354912e371ae9
Source dataset
uspto-grants-2014_04
Patent number
US08697873B2

Reaction notes

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