tert-Butyl (3-aminopropyl)carbamate → 4-[3-(Tert-butoxycarbonylamino)propylamino]-2-chloro-3-nitroquinoline

HRID 1108628Notes

Reaction equation

HRID 1108628 reaction equation
[Cl:1][C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[C:10](Cl)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[C:16]([O:20][C:21]([NH:23][CH2:24][CH2:25][CH2:26][NH2:27])=[O:22])([CH3:19])([CH3:18])[CH3:17]>C(N(CC)CC)C>[C:16]([O:20][C:21]([NH:23][CH2:24][CH2:25][CH2:26][NH:27][C:10]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=[C:2]([Cl:1])[C:11]=1[N+:12]([O-:14])=[O:13])=[O:22])([CH3:19])([CH3:18])[CH3:17]

Participants

4

Reactant 2

HCID 2735700tert-Butyl (3-aminopropyl)carbamateHCID 27851382,4-Dichloro-3-nitroquinoline

Product 1

HCID 187839794-[3-(Tert-butoxycarbonylamino)propylamino]-2-chloro-3-nitroquinolineYield 66.4%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

0.59 g (2.41 mmol) of 2,4-Dichloro-3-nitroquinoline and 0.42 g (2.41 mmol) of N-(tert-butoxycarbonyl)-1,3-propanediamine were heated at 70° C. in 10 ml of triethylamine and stirred for 1.5 hours. Triethylamine was distilled off under reduced pressure. The resulting residue was dissolved in methylene chloride, washed with water, and dried (Na2SO4). After the solvent was distilled off under reduced pressure, the residue was triturated with methanol and filtered to obtain 0.61 g (1.60 mmol) of 4-[3-(tert-butoxycarbonylamino)propylamino]-2-chloro-3-nitroquinoline shown below as yellow crystals (mp: 159-161° C.). ##STR34## Its spectroscopic data are as follows: IR (KBr) cm-1 : 3310, 1680, 1580. 1H-NMR (CDCl3) δ (ppm) : 1.50 (9H, s), 1.77 (2H, m), 3.27 (2H, q, J=6.1 Hz), 3.36 (2H, q, J=6.0 Hz), 4.82 (1 H, br), 7.37 (1H, br), 7.55 (1H, t, J=7.8 Hz), 7.72 (1H, t, J=7.7 Hz), 7.89 (1H, d, J=8.2 Hz), 8.27 (1H, d, J=8.4 Hz).

Workup

  1. distillationTriethylamine was distilled off under reduced pressure
  2. dissolutionThe resulting residue was dissolved in methylene chloride
  3. washwashed with water
  4. dry with materialdried (Na2SO4)
  5. distillationAfter the solvent was distilled off under reduced pressure
  6. customthe residue was triturated with methanol
  7. filtrationfiltered

Sources & evidence

ORD record
ord-453f3eb39f0b4ae78a4d76ad5b18ccce
Source dataset
uspto-grants-2000_05
Patent number
US06069149

Reaction notes

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