Ammonium formate → HCID 10681198, compound

HRID 1274119Notes

Reaction equation

HRID 1274119 reaction equation
C([O-])=O.[NH4+].[CH3:5][O:6][C:7](=[O:28])[C:8]1[CH:13]=[CH:12][C:11]([NH:14][CH:15]2[CH2:20][CH2:19][N:18](CC3C=CC=CC=3)[CH2:17][CH2:16]2)=[CH:10][CH:9]=1>C(O)C>[CH3:5][O:6][C:7](=[O:28])[C:8]1[CH:9]=[CH:10][C:11]([NH:14][CH:15]2[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]2)=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 2723923Ammonium formateHCID 10520033HCID 10520033, compound

Product 1

HCID 10681198HCID 10681198, compoundYield 94.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

Ammonium formate (4.2 g, 66 mmol) was added to a solution of 46 (2.3 g, 6.9 mmol) in 100 mL of absolute ethanol. The mixture was purged with argon then palladium (0.8 g, 5% on activated carbon) was added. The resulting mixture was heated to 80° C. and maintained at that temperature for 12 h. After cooling to 25° C., the mixture was filtered through celite and the filtrate was concentrated under reduced pressure. The residue was cooled to 0° C., saturated NaHCO3 (100 mL) was added and the resulting mixture was stirred for 30 min. The aqueous layer was extracted with EtOAc (3×100 mL). The combined organic layers were dried (Na2SO4), filtered, and concentrated in vacuo to give 1.53 g (94%) of the title compound: TLC (Rf =0.20; 15% MeOH/CH2Cl2); 1H NMR (CDCl3) δ 7.85 (d, 2H, J=8.8), 6.54 (d, 2H, J=8.8), 4.08 (d, 1H, J=7.6), 3.85 (s, 3H), 3.47 (m, 1H), 3.13 (d, 2H, J=12.8), 2.72 (t, 2H, J=11.9), 2.07 (d, 2H, J=2.1), 1.37 (m, 2H); 13C NMR (CDCl3) δ 167.3, 150.7, 131.6, 118.0, 111.7, 51.5, 49.9, 45.4, 33.6; Anal. (C13H18N2O2 ·1/4 H2O·1/2 CH3OH) C, H, N.

Workup

  1. customThe mixture was purged with argon
  2. additionpalladium (0.8 g, 5% on activated carbon) was added
  3. temperaturemaintained at that temperature for 12 h
  4. temperatureAfter cooling to 25° C.
  5. filtrationthe mixture was filtered through celite
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. temperatureThe residue was cooled to 0° C.
  8. additionsaturated NaHCO3 (100 mL) was added
  9. extractionThe aqueous layer was extracted with EtOAc (3×100 mL)
  10. dry with materialThe combined organic layers were dried (Na2SO4)
  11. filtrationfiltered
  12. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-67fbe4d8ac674751823cbdaa29d76a52
Source dataset
uspto-grants-2000_12
Patent number
US06156758

Reaction notes

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