Methanol → tert-Butyl (4-((3-aminoquinolin-4-yl)amino)butyl)carbamate

HRID 1108643Notes

Reaction equation

HRID 1108643 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]=[CH:16][C:15]=1[N+:24]([O-])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].CO>[C].[Pd].C(OCC)(=O)C>[NH2:24][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

5

Reactant 2

HCID 887MethanolHCID 22381766tert-Butyl (4-((3-nitroquinolin-4-yl)amino)butyl)carbamate

Product 1

HCID 18783942tert-Butyl (4-((3-aminoquinolin-4-yl)amino)butyl)carbamateYield 69.6%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

1.80 g (5.0 mmol) of 4-[4-(tert-butoxycarbonylamino) butylamino]-3-nitroquinoline) was dissolved to a mixed solvent of 30 ml of methanol and 10 ml of ethyl acetate. 0.5 g of 10% palladium-carbon was added thereto and the mixture was stirred overnight under hydrogen atomosphere. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:methanol=50:1 to 10:1 (v/v)) to obtain 1.15 g (3.48 mmol) of 3-amino-4-[4-(tert-butoxycarbonylamino)butylamino]quinoline shown below as a brown amorphous substance. ##STR52## Its physicochemical properties were in agreement with those of the compound of Example 22.

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=50:1 to 10:1 (v/v))

Sources & evidence

ORD record
ord-ea3177d27480469f89e4f64b698ddaff
Source dataset
uspto-grants-2000_05
Patent number
US06069149

Reaction notes

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