4-nitro-N-[2-(3-pyridin-3-ylpropoxy)ethyl]tetrazolo[1,5-a]quinolin-5-amine → N5-[2-(3-pyridin-3-ylpropoxy)ethyl]tetrazolo[1,5-a]quinoline-4,5-diamine

HRID 432701Notes

Reaction equation

HRID 432701 reaction equation
[N+:1]([C:4]1[C:5]2[N:6]([N:27]=[N:28][N:29]=2)[C:7]2[C:12]([C:13]=1[NH:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][CH2:20][C:21]1[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2)([O-])=O.[H][H]>[Pt].C(O)C>[N:23]1[CH:24]=[CH:25][CH:26]=[C:21]([CH2:20][CH2:19][CH2:18][O:17][CH2:16][CH2:15][NH:14][C:13]2[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[N:6]3[N:27]=[N:28][N:29]=[C:5]3[C:4]=2[NH2:1])[CH:22]=1

Participants

5

Reactant 2

HCID 187601944-nitro-N-[2-(3-pyridin-3-ylpropoxy)ethyl]tetrazolo[1,5-a]quinolin-5-amineHCID 178418361HCID 178418361, compound

Product 1

HCID 18760199N5-[2-(3-pyridin-3-ylpropoxy)ethyl]tetrazolo[1,5-a]quinoline-4,5-diamineYield 97.2%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 702EthanolSolvent

Procedure

4-Nitro-N-[2-(3-pyridin-3-ylpropoxy)ethyl]tetrazolo[1,5-a]quinolin-5-amine (34.3 g, 87.2 mmol) was added to a 3 liter stainless steel pressure flask containing ethanol (1.25 L, absolute). Platinum on carbon (3.00 g, 5% w/w) was added and the flask was placed on a Parr hydrogenation apparatus. The reaction was shaken under 45 psi (3.15 Kg/cm2) of hydrogen for 24 hours. The catalyst was removed by filtration through Celite™ and the Celite pad was washed with several portions of ethanol. The filtrate was concentrated in vacuo to provide 30.8 g of N5-[2-(3-pyridin-3-ylpropoxy)ethyl]tetrazolo[1,5-a]quinoline-4,5-diamine as an orange/red oil. MS (CI) m/e 364 (MH+), 336.

Workup

  1. customThe catalyst was removed by filtration through Celite™
  2. washthe Celite pad was washed with several portions of ethanol
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-df0481b3fbf94f0f96bb721e6ee10ca3
Source dataset
uspto-grants-2003_12
Patent number
US06664260B2

Reaction notes

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