Ammonia → HCID 18783990, compound

HRID 1108636Notes

Reaction equation

HRID 1108636 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].[Sn](Cl)(Cl)(Cl)Cl.N>C(O)C>[NH2:25][C:15]1[C:16]([Cl:24])=[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]([CH3:3])([CH3:2])[CH3:4])=[O:7])=[CH:22][CH:21]=[CH:20][CH:19]=2

Participants

5

Reactant 3

HCID 222AmmoniaHCID 24287Tin tetrachlorideHCID 18783946HCID 18783946, compound

Product 1

HCID 18783990HCID 18783990, compoundYield 25.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.5 g (1.27 mmol) of 4-[4-(tert-Butoxycarbonylamino)butylamino]-2-chloro-3-nitroquinoline was dissolved in 13 ml of ethanol. 1.0 g (4.43 mmol) of tin chloride [II] dihydrate was added thereto and the mixture was refluxed under heating for one hour. The reaction mixture was poured into 2N aqueous ammonia. The resulting solution was extracted twice with chloroform, washed (brine), and dried (Na2SO4). The solvent was distilled off under reduce pressure and the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1 (v/v)) to collect the product. After the solvent was distilled off, the resulting product was triturated with diethyl ether to obtain 0.12 g (0.329 mmol) of 3-amino-4-[4-(tert-butoxycarbonylamino)butylamino]-2-chloroquinoline shown below as orange crystals. ##STR42## Its spectroscopic data are as follows: IR (KBr) cm- : 3270, 1680, 1540, 760. 1H-NMR (CDCl3) δ (ppm) : 1.44 (9H, s), 1.64 (4H, m), 3.17 (2H, q, J=6.0 Hz), 3.27 (2H, t, J=6.6 Hz), 3.89 (1H, H, br), 4.15 (2H, br), 4.59 (1H, br), 7.47 (2H, m), 7.77 (1H, d, J=7.6 Hz), 7.89 (1H, d, J=7.2 Hz).

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating for one hour
  3. extractionThe resulting solution was extracted twice with chloroform
  4. washwashed (brine)
  5. dry with materialdried (Na2SO4)
  6. distillationThe solvent was distilled off
  7. customthe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1 (v/v))
  8. customto collect the product
  9. distillationAfter the solvent was distilled off
  10. customthe resulting product was triturated with diethyl ether

Sources & evidence

ORD record
ord-c3175b4206e54135a5a22489bae06750
Source dataset
uspto-grants-2000_05
Patent number
US06069149

Reaction notes

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