Dichloromethane → 4-nitro-N-[2-(3-pyridin-3-ylpropoxy)ethyl]tetrazolo[1,5-a]quinolin-5-amine

HRID 432700Notes

Reaction equation

HRID 432700 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]2[N:12]=[N:13][N:14]=[C:4]2[C:3]=1[N+:15]([O-:17])=[O:16].ClCCl.C(N(CC)CC)C.[N:28]1[CH:33]=[CH:32][CH:31]=[C:30]([CH2:34][CH2:35][CH2:36][O:37][CH2:38][CH2:39][NH2:40])[CH:29]=1>C(O)C>[N+:15]([C:3]1[C:4]2[N:5]([N:12]=[N:13][N:14]=2)[C:6]2[C:11]([C:2]=1[NH:40][CH2:39][CH2:38][O:37][CH2:36][CH2:35][CH2:34][C:30]1[CH:29]=[N:28][CH:33]=[CH:32][CH:31]=1)=[CH:10][CH:9]=[CH:8][CH:7]=2)([O-:17])=[O:16]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 27868695-Chloro-4-nitrotetrazolo[1,5-a]quinolineHCID 219130212-(3-Pyridin-3-ylpropoxy)ethanamine

Product 1

HCID 187601944-nitro-N-[2-(3-pyridin-3-ylpropoxy)ethyl]tetrazolo[1,5-a]quinolin-5-amineYield 79.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

5-Chloro-4-nitrotetrazolo[1,5-a]quinoline (28.86 g, 0.11 mol), dichloromethane (600 ml), and triethylamine (21.14 ml, 0.11 mol) were combined and the resulting solution was chilled to 0° C. 2-(3-Pyridin-3-ylpropoxy)ethylamine (22.9 g, 0.13 mol) was added dropwise. The reaction was allowed to slowly warm to room temperature, then stirred at room temperature for 1 hour and finally at reflux for 2 hours. The reaction was cooled to room temperature and then quenched with water (200 ml). The phases were separated and the aqueous layer was extracted with dichloromethane (3×50 ml). The combined organic fractions were washed with brine (100 ml), dried (Na2SO4), filtered and concentrated to yield a yellow solid. The solid was slurried in ethanol (150 ml) and filtered to provide 34.3 g of 4-nitro-N-[2-(3-pyridin-3-ylpropoxy)ethyl]tetrazolo[1,5-a]quinolin-5-amine.

Workup

  1. temperatureto slowly warm to room temperature
  2. temperaturefinally at reflux for 2 hours
  3. temperatureThe reaction was cooled to room temperature
  4. customquenched with water (200 ml)
  5. customThe phases were separated
  6. extractionthe aqueous layer was extracted with dichloromethane (3×50 ml)
  7. washThe combined organic fractions were washed with brine (100 ml)
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customto yield a yellow solid
  12. filtrationfiltered

Sources & evidence

ORD record
ord-aad48e0c8e3a4d29ac6b952cce99320f
Source dataset
uspto-grants-2003_12
Patent number
US06664260B2

Reaction notes

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