Methanol → HCID 11550312, compound

HRID 496294Notes

Reaction equation

HRID 496294 reaction equation
[CH3:1][CH:2]([CH3:18])[CH2:3][NH:4][C:5]1[CH:10]=[C:9]([CH3:11])[N:8]2[N:12]=[N:13][N:14]=[C:7]2[C:6]=1[N+:15]([O-])=O.CO>C1(C)C=CC=CC=1>[CH3:1][CH:2]([CH3:18])[CH2:3][NH:4][C:5]1[CH:10]=[C:9]([CH3:11])[N:8]2[N:12]=[N:13][N:14]=[C:7]2[C:6]=1[NH2:15]

Participants

4

Reactant 2

HCID 887MethanolHCID 11499770HCID 11499770, compound

Product 1

HCID 11550312HCID 11550312, compoundYield 88.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

N-(2-Methylpropyl)-5-methyl-8-nitrotetraazolo[1,5-α]pyridin-7-amine (9.60 g, 43.6 mmol) was dissolved in warm anhydrous toluene (900 mL) and methanol (100 mL) and then added to a 2 L stainless steel Parr vessel. The vessel was flushed several times with nitrogen, and 5% platinum on carbon (2.0 g) was added to the solution. The vessel was flushed multiple times with hydrogen, and then placed under hydrogen pressure (50 psi, 3.4×105 Pa). After two hours, no further hydrogen was consumed. The reaction mixture was filtered through a layer of filter agent (available from Aldrich, Milwaukee, Wis. under the trade name CELITE), and the filter cake was washed with hot toluene (1 L). The filtrate was concentrated under reduced pressure to yield 8.5 g N7-(2-methylpropyl)-5-methyltetraazolo[1,5-α]pyridine-7,8-diamine as a light orange solid, m.p. 159-162° C.

Workup

  1. customThe vessel was flushed several times with nitrogen, and 5% platinum on carbon (2.0 g)
  2. additionwas added to the solution
  3. customThe vessel was flushed multiple times with hydrogen
  4. customno further hydrogen was consumed
  5. filtrationThe reaction mixture was filtered through a layer of filter agent (available from Aldrich, Milwaukee, Wis
  6. washunder the trade name CELITE), and the filter cake was washed with hot toluene (1 L)
  7. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-c0db85630c424c9f8414183fbfd04d6a
Source dataset
uspto-grants-2005_09
Patent number
US06943255B2

Reaction notes

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