HCID 18783946, compound → HCID 18783941, compound

HRID 1108648Notes

Reaction equation

HRID 1108648 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][NH:13][C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[N:17]=[C:16]([Cl:24])[C:15]=1[N+:25]([O-])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[C].[Pd]>[ClH:24].[NH2:25][C:15]1[CH:16]=[N:17][C:18]2[C:23]([C:14]=1[NH:13][CH2:12][CH2:11][CH2:10][CH2:9][NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])=[CH:22][CH:21]=[CH:20][CH:19]=2

Participants

4

Reactant 1

HCID 18783946HCID 18783946, compound

Product 1

HCID 18783941HCID 18783941, compoundYield 75.4%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

2.50 g (6.33 mmol) of 4-[4-(tert-Butoxycarbonylamino)butylamino]-2-chloro-3-nitroquinoline was dissolved in 65 ml of methanol and 1 g of 10% palladium-carbon was added thereto. The mixture was stirred for one day under hydrogen atomosphere. The reaction mixture was filtered, the filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (chloroform:methanol=10:1 (v/v)). Finally, the resulting product was triturated with diethyl ether and collected by filtration to obtain 1.75 g (4.77 mmol) of 3-amino-4-[4-(tert-butoxycarbonylamino)butylamino]quinoline hydrochloride shown below as a yellow solid. ##STR57## Its spectroscopic data are as follows: IR (KBr) cm-1 : 3340, 2970, 1690, 1590, 1530, 1170.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (chloroform:methanol=10:1 (v/v))
  4. customFinally, the resulting product was triturated with diethyl ether
  5. filtrationcollected by filtration

Sources & evidence

ORD record
ord-82244d514bbf4a1bb2e4af4cd130412c
Source dataset
uspto-grants-2000_05
Patent number
US06069149

Reaction notes

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