Hydrochloric Acid → 3-Amino-4-[3-(benzyloxycarbonylamino)propylamino]-2-chloroquinoline

HRID 1108625Notes

Reaction equation

HRID 1108625 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][CH2:14][NH:15][C:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[N:19]=[C:18]([Cl:26])[C:17]=1[N+:27]([O-])=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.C(=O)([O-])O.[Na+]>CO.[Fe]>[NH2:27][C:17]1[C:18]([Cl:26])=[N:19][C:20]2[C:25]([C:16]=1[NH:15][CH2:14][CH2:13][CH2:12][NH:11][C:9]([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:10])=[CH:24][CH:23]=[CH:22][CH:21]=2

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 187839664-[3-(Benzyloxycarbonylamino)propylamino]-2-chloro-3-nitroquinoline

Product 1

HCID 187839713-Amino-4-[3-(benzyloxycarbonylamino)propylamino]-2-chloroquinolineYield 47.9%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 887MethanolSolvent

Procedure

0.27 g (0.651 mmol) of 4-[3-(benzyloxycarbonylamino)propylamino]-2-chloro-3-nitroquinoline was dissolved in 10 ml of methanol. One ml of concentrated hydrochloric acid and 0.22 g (0.390 mmol) of iron powder were added thereto and the mixture was stirred at room temperature for 2 hours. The reaction mixture was poured into a saturated sodium hydrogencarbonate aqueous solution. After the resulting mixed solution was extracted with ethyl acetate, the extract was washed with brine and dried (Na2SO4). The solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography (chloroform:methanol=300:1 (v/v)) to obtain 0.12 g (0.312 mmol) of 3-amino-4-[3-(benzyloxycarbonylamino)propylamino]-2-chloroquinoline shown below as faint yellow powder. ##STR30## Its spectroscopic data are as follows: 1H-NMR (CDCl3) δ (ppm) :1.76 (2H, m), 3.30 (2H, m), 3.42 (2H, q, J=6.3 Hz), 4.21 (2H, b r), 4.44 (1H, br), 4.92 (1H, br), 5.16 (2H, s), 7.30~7.39 (5H, m), 7.46 (2H, m), 7.89 (2H, m).

Workup

  1. additionAfter the resulting mixed solution
  2. extractionwas extracted with ethyl acetate
  3. washthe extract was washed with brine
  4. dry with materialdried (Na2SO4)
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (chloroform:methanol=300:1 (v/v))

Sources & evidence

ORD record
ord-bc3dcd04d8c8482a85b7e7727cbd4f03
Source dataset
uspto-grants-2000_05
Patent number
US06069149

Reaction notes

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