Ammonia → 3-Amino-4-[3-(tert-butoxycarbonylamino)propylamino]-2-chloro-quinoline

HRID 1108629Notes

Reaction equation

HRID 1108629 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][NH:12][C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]=[C:15]([Cl:23])[C:14]=1[N+:24]([O-])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Sn](Cl)(Cl)(Cl)Cl.N>C(O)C>[NH2:24][C:14]1[C:15]([Cl:23])=[N:16][C:17]2[C:22]([C:13]=1[NH:12][CH2:11][CH2:10][CH2:9][NH:8][C:6]([O:5][C:1]([CH3:3])([CH3:2])[CH3:4])=[O:7])=[CH:21][CH:20]=[CH:19][CH:18]=2

Participants

5

Reactant 3

HCID 222AmmoniaHCID 24287Tin tetrachlorideHCID 187839794-[3-(Tert-butoxycarbonylamino)propylamino]-2-chloro-3-nitroquinoline

Product 1

HCID 187839403-Amino-4-[3-(tert-butoxycarbonylamino)propylamino]-2-chloro-quinolineYield 61.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.27 g (0.70 mmol) of 4-[3-(tert-Butoxycarbonylamino)propylamino]-2-chloro-3-nitroquinoline was dissolved in 7 ml of ethanol. Tin chloride [II] dihydrate (0.55 g, 2.45 mmol) was added thereto and the mixture was refluxed under heating for 1 hour. After cooling, the reaction mixture was poured into 2N aqueous ammonia. The resulting solution was extracted twice with chloroform, thereafter the extract was washed (brine), and dried (Na2SO4). The solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1 (v/v)) to obtain 0.15 g (0.428 mmol) of 3-amino-4-[3-(tert-butoxycarbonylamino)propylamino]-2-chloro-quinoline shown below as pale yellow crystals. ##STR35## Its spectroscopic data are as follows: 1H-NMR (CDCl3) δ (ppm) : 1.49 (9H, s), 1.73 (2H, m), 3.29 (2H, t, J=6.2 Hz), 3.35 (2H, q, J=6.0 Hz), 4.28 (2H, br), 4.60 (1H, br), 4.75 (1H, br), 7.44 (2H, m), 7.87 (1H, d, J=7.6 Hz), 7.94 (1H, d, J=7.6 Hz).

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating for 1 hour
  3. temperatureAfter cooling
  4. extractionThe resulting solution was extracted twice with chloroform
  5. washthe extract was washed (brine)
  6. dry with materialdried (Na2SO4)
  7. distillationThe solvent was distilled off under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1 (v/v))

Sources & evidence

ORD record
ord-1953144ce4e74aa9ad268d3db8546ad5
Source dataset
uspto-grants-2000_05
Patent number
US06069149

Reaction notes

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