Acetic Anhydride → HCID 178474658, compound

HRID 887805Notes

Reaction equation

HRID 887805 reaction equation
C([N:8]1[C:12]2[CH:13]=[CH:14][C:15]3[CH2:16][CH2:17][C:18](=[CH:20][C:21]#[N:22])[C:19]=3[C:11]=2[N:10]=[C:9]1[CH3:23])C1C=CC=CC=1.C(N(CC)CC)C.[C:31](OC(=O)C)(=[O:33])[CH3:32]>N.C(O)C.[Co]>[CH3:23][C:9]1[NH:10][C:11]2[C:19]3[CH:18]([CH2:20][CH2:21][NH:22][C:31](=[O:33])[CH3:32])[CH2:17][CH2:16][C:15]=3[CH:14]=[CH:13][C:12]=2[N:8]=1

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 68698101HCID 68698101, compound

Product 1

HCID 178474658HCID 178474658, compoundYield 31%

Reagents, catalysts & solvents 2

HCID 104730CobaltCatalystHCID 22020343Ethanol, reaction products with ammonia, distn. residuesSolvent

Procedure

(3-Benzyl-2-methyl-6,7-dihydroindeno[4,5-d]imidazol-8(3H)-ylidene)acetonitrile was dissolved in 2M ammonia/ethanol solution (14 mL), Raney cobalt (10 g) was added, and the mixture was stirred under a hydrogen atmosphere at room temperature for 14 hr. The catalyst was filtered off through celite, and the filtrate was concentrated under reduced pressure. The residue was dissolved in tetrahydrofuran (3 mL), triethylamine (34.9 μL, 0.25 mmol) and acetic anhydride (18.9 μL, 0.20 mmol) were added, and the mixture was stirred at room temperature for 30 min. The reaction solution was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (methanol/ethyl acetate=5/95→15/85). The purified product was dissolved in methanol (3 mL), palladium-carbon powder (20 mg) was added, and the mixture was stirred under a hydrogen atmosphere at room temperature for 5 hr. The catalyst was filtered off, and the filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (methanol/ethyl acetate=5/95→20/80) to give the title compound (13.4 mg, yield 31%).

Workup

  1. filtrationThe catalyst was filtered off through celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. dissolutionThe residue was dissolved in tetrahydrofuran (3 mL)
  4. stirringthe mixture was stirred at room temperature for 30 min
  5. concentrationThe reaction solution was concentrated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (methanol/ethyl acetate=5/95→15/85)
  7. dissolutionThe purified product was dissolved in methanol (3 mL)
  8. additionpalladium-carbon powder (20 mg) was added
  9. stirringthe mixture was stirred under a hydrogen atmosphere at room temperature for 5 hr
  10. filtrationThe catalyst was filtered off
  11. concentrationthe filtrate was concentrated under reduced pressure
  12. customthe residue was purified by silica gel column chromatography (methanol/ethyl acetate=5/95→20/80)

Sources & evidence

ORD record
ord-71387da4191142bba7de8cb403452343
Source dataset
uspto-grants-2012_08
Patent number
US08247429B2

Reaction notes

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