Hydrochloric Acid → HCID 59679857, compound

HRID 1667056Notes

Reaction equation

HRID 1667056 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[N:11]=[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]2[CH:18]=1)([O-])=O.C(O)C.Cl>[Pd].O>[N:11]1[C:10]([C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH2:1])=[CH:18][N:13]2[CH2:14][CH2:15][CH2:16][CH2:17][C:12]=12

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 596799982-(2-Nitrophenyl)imidazo[1,2-a]pyridine

Product 1

HCID 59679857HCID 59679857, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

In a dry flask was charged 2-(2-Nitro-phenyl)-imidazo[1,2-a]pyridine (239 mg, 1 mmol), 10% Pd/C (15 mg), Ethanol (25 ml), water (1.5 ml) and 4M HCl (0.5 ml). The atmosphere was flushed with nitrogen and stirred over 1 atm. hydrogen over 5 days with an additional charge of Pd/C catalyst (15 mg) and 4 N HCl (4.5 ml) until reaction completion was obtained. The reaction mixture was filtered through Celite, and neutralized to pH=6 with a saturated NaHCO3 solution. The solution was roto-evaporated to remove the ethanol, the aqueous layer was extracted with CH2Cl2 (2×5 ml), and the combined organic layer dried over Na2SO4 and concentrated to obtain the product as an oil in quantitative yield (205 mg). (MS, M++H=214.1)

Workup

  1. customThe atmosphere was flushed with nitrogen
  2. additionan additional charge of Pd/C catalyst (15 mg) and 4 N HCl (4.5 ml) until reaction completion
  3. customwas obtained
  4. filtrationThe reaction mixture was filtered through Celite
  5. customThe solution was roto-evaporated
  6. customto remove the ethanol
  7. extractionthe aqueous layer was extracted with CH2Cl2 (2×5 ml)
  8. dry with materialthe combined organic layer dried over Na2SO4
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-c5b54983d40841ee881610607ec5d46a
Source dataset
uspto-grants-2011_10
Patent number
US08044198B2

Reaction notes

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