Ammonium formate → HCID 22619636, compound

HRID 840502Notes

Reaction equation

HRID 840502 reaction equation
[CH3:1][N:2]([CH3:24])[CH2:3][CH2:4][CH2:5][C:6]1(O)[C:12]2[CH:13]=[CH:14][C:15]([O:17][CH3:18])=[CH:16][C:11]=2[CH2:10][CH2:9][C:8]2[CH:19]=[CH:20][CH:21]=[CH:22][C:7]1=2.C([O-])=O.[NH4+]>[Pd].C(O)(=O)C>[CH3:18][O:17][C:15]1[CH:14]=[CH:13][C:12]2[CH:6]([CH2:5][CH2:4][CH2:3][N:2]([CH3:1])[CH3:24])[C:7]3[CH:22]=[CH:21][CH:20]=[CH:19][C:8]=3[CH2:9][CH2:10][C:11]=2[CH:16]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 22619642HCID 22619642, compound

Product 1

HCID 22619636HCID 22619636, compoundYield 84.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

To 65 mg (0.19 mmol) of 4 was added 5 ml of glacial acetic acid. The mixture was heated to 60° C. and allowed to stir until the mixture was homogeneous. The reaction mixture was cooled to room temperature and 300 mg of 10% Pd/C was added followed by 1 g of ammonium formate. The mixture was heated to 70° C. and allowed to stir at that temperature for 4 hours. The reaction mixture was cooled to room temperature and filtered. The residue was washed with 50 ml of dichloromethane. The combined filtrate was concentrated. The residue was dissolved in 100 ml of dichloromethane and washed with 2×50 ml of saturated NaHCO3 followed by 2×50 ml of brine. The organic part was dried (Na2SO4) and concentrated to give 50 mg (0.16 mmol, 82%) of 5.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. temperatureThe mixture was heated to 70° C.
  3. stirringto stir at that temperature for 4 hours
  4. temperatureThe reaction mixture was cooled to room temperature
  5. filtrationfiltered
  6. washThe residue was washed with 50 ml of dichloromethane
  7. concentrationThe combined filtrate was concentrated
  8. dissolutionThe residue was dissolved in 100 ml of dichloromethane
  9. washwashed with 2×50 ml of saturated NaHCO3
  10. dry with materialThe organic part was dried (Na2SO4)
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-2138c36f950944cc90a2276096e6da3f
Source dataset
uspto-grants-2002_04
Patent number
US06368814B1

Reaction notes

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