Ammonium formate → 2-Amino-4-(4,5-dihydro-1h-imidazol-2-yl)phenol

HRID 1019645Notes

Reaction equation

HRID 1019645 reaction equation
[CH2:1]1[NH:15][C:4](=[C:5]2[CH:11]=[C:10]([N+:12]([O-])=O)[C:8](=[O:9])[CH:7]=[CH:6]2)[NH:3][CH2:2]1.C([O-])=O.[NH4+]>CO.[Pd]>[NH2:12][C:10]1[CH:11]=[C:5]([C:4]2[NH:15][CH2:1][CH2:2][N:3]=2)[CH:6]=[CH:7][C:8]=1[OH:9]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 178515904HCID 178515904, compound

Product 1

HCID 1361479112-Amino-4-(4,5-dihydro-1h-imidazol-2-yl)phenolYield 74%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of the cyclic amidine 35 (490 mg, 2.36 mmol), ammonium formate (1.5 g, 23.6 mmol) and 10% Pd on carbon (50 mg) in methanol was heated at reflux for 4 hrs. After cooling to room temperature, the catalyst was removed by filtration through celite and the filtrate was concentrated in vacuo. The residue was triturated with hexane and the resulting solid was collected to yield 309 mg (74%) of the desired product 37. 1H NMR (600 MHz, DMSO-d6) δ 7.07 (d, 1H, J=1.8 Hz), 6.94 (dd, 1H, J=7.8, 1.8 Hz), 6.64 (d, 1H, J=7.8 Hz), 5.46 (br s, 2H), 4.69 (br s, 1H), 2.64 (s, 4H). MS: m/z Calcd 177.2 Found MH+ 173.3

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 4 hrs
  3. customthe catalyst was removed by filtration through celite
  4. concentrationthe filtrate was concentrated in vacuo
  5. customThe residue was triturated with hexane
  6. customthe resulting solid was collected

Sources & evidence

ORD record
ord-feecb08c18d949b38e84b0e861a4c2b8
Source dataset
uspto-grants-2014_05
Patent number
US08716283B2

Reaction notes

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