Toluene → HCID 69410832, compound

HRID 1245994Notes

Reaction equation

HRID 1245994 reaction equation
[CH3:1][C:2]1[N:7]2[N:8]=[N:9][N:10]=[C:6]2[C:5]([N+:11]([O-])=O)=[C:4]([NH:14][CH2:15][CH2:16][O:17][C:18](=[O:20])[CH3:19])[C:3]=1[CH3:21].C1(C)C=CC=CC=1>[Pt].CC(O)C>[NH2:11][C:5]1[C:6]2[N:7]([N:8]=[N:9][N:10]=2)[C:2]([CH3:1])=[C:3]([CH3:21])[C:4]=1[NH:14][CH2:15][CH2:16][O:17][C:18](=[O:20])[CH3:19]

Participants

5

Reactant 2

HCID 1140TolueneHCID 69193040HCID 69193040, compound

Product 1

HCID 69410832HCID 69410832, compoundYield 91.3%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 3776IsopropanolSolvent

Procedure

A Parr vessel was charged with acetic acid 2-[(5,6-dimethyl-8-nitrotetrazolo[1,5-a]pyridin-7-yl)amino]ethyl ester (50.0 g, 170 mmol), 5% platinum on carbon (5.00 g), toluene (600 mL), and 2-propanol (50 mL) and purged with nitrogen. The vessel was then placed under hydrogen pressure (20 psi,) for 20 hours at room temperature. The reaction mixture was filtered through a layer of CELITE filter aid, and the filter cake was washed with 90:10 dichloromethane:methanol. The filtrate was concentrated under reduced pressure to provide a dark gray solid, which was triturated with diethyl ether, isolated by filtration, and dried to provide 41.0 g of acetic acid 2-[(8-amino-5,6-dimethyltetrazolo[1,5-a]pyridin-7-yl)amino]ethyl ester as a light gray solid.

Workup

  1. custompurged with nitrogen
  2. customfor 20 hours
  3. customat room temperature
  4. filtrationThe reaction mixture was filtered through a layer of CELITE
  5. filtrationfilter aid
  6. washthe filter cake was washed with 90:10 dichloromethane
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. customto provide a dark gray solid, which
  9. customwas triturated with diethyl ether
  10. customisolated by filtration
  11. customdried

Sources & evidence

ORD record
ord-5ee4e7ad13f242a99609de458f75f975
Source dataset
uspto-grants-2006_10
Patent number
US07125890B2

Reaction notes

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