HCID 67228436, compound → HCID 67227906, compound

HRID 2383166Notes

Reaction equation

HRID 2383166 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[N:15]1[N:19]=[N:20][N:21]=[C:14]1[C:13]([N+:22]([O-])=O)=[C:12]2[NH:25][CH2:26][CH:27]([CH3:29])[CH3:28])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H][H]>C(#N)C.[Pt]>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[N:15]1[N:19]=[N:20][N:21]=[C:14]1[C:13]([NH2:22])=[C:12]2[NH:25][CH2:26][CH:27]([CH3:29])[CH3:28])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 67228436HCID 67228436, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67227906HCID 67227906, compoundYield 82.6%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 6342AcetonitrileSolvent

Procedure

7-(Benzyloxy)-N-(2-methylpropyl)-4-nitrotetraazolo[1,5-a]quinolin-5-amine (10 g, 25.4 mmol) was shaken in 200 mL of acetonitrile with 5% platinum on carbon (1 g) under 50 psi (3.45×105 Pa) of hydrogen. After 5 hours, the mixture was filtered through CELITE filter agent. Some product was isolated as a solid on the top of the filter cake. This solid was collected, dissolved in warm DMF, and filtered again through fresh CELITE filter agent. The combined filtrates were cooled and allowed to sit overnight. The resulting precipitate was collected in 2 crops to yield 7.6 g of 7-(benzyloxy)-N5-(2-methylpropyl)tetraazolo[1,5-a]quinoline-4,5-diamine as a brown solid.

Workup

  1. filtrationthe mixture was filtered through CELITE
  2. filtrationfilter agent
  3. customSome product was isolated as a solid on the top of the filter cake
  4. customThis solid was collected
  5. dissolutiondissolved in warm DMF
  6. filtrationfiltered again through fresh CELITE
  7. filtrationfilter agent
  8. temperatureThe combined filtrates were cooled
  9. waitto sit overnight
  10. customThe resulting precipitate was collected in 2 crops

Sources & evidence

ORD record
ord-c4d473c124c440fea268574aac6635ac
Source dataset
uspto-grants-2012_09
Patent number
US08263594B2

Reaction notes

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