Ammonium formate → HCID 10752245, compound

HRID 1274127Notes

Reaction equation

HRID 1274127 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)=[N:10][CH:9]=1>C(O)C>[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][NH:18][CH2:17][CH2:16]2)=[N:10][CH:9]=1

Participants

4

Reactant 2

HCID 2723923Ammonium formateHCID 10520108HCID 10520108, compound

Product 1

HCID 10752245HCID 10752245, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

Ammonium formate (4.9 g, 67.2 mmol) was added to a solution of (39) (4.2 g, 12.9 mmol) in 100 mL of absolute ethanol. The mixture was purged with argon then palladium (0.9 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 in vacuo. The residue was cooled to 0° C. and saturated Na2CO3 (100 mL) was added. The resulting mixture was stirred for 30 min at 0° C. then was extracted with EtOAc (3×50 mL). The combined organic layers were dried (Na2SO4), filtered, and concentrated in vacuo to give 2.6 g (86%) of the title compound; 1H NMR (CDCl3) δ 8.55 (s, 1H), 7.78 (d, 1H, J=8.9), 7.35 (d, 1H, J=7.3), 6.49 (d, 1H, J=8.9), 3.77 (m, 4H), 3.12 (s, 1H), 2.94 (m, 2H), 2.52 (m, 2H), 1.82 (m, 2H), 1.29 (m, 2H); 13C NMR (CDCl3) δ 165.7, 160.2, 150.8, 136.7, 112.7, 107.5, 51.1, 48.0, 45.0, 33.0; HRMS (FAB) m/z 236.1392 (M+H)+ (C12H17N3O2, requires 236.1399).

Workup

  1. customThe mixture was purged with argon
  2. additionpalladium (0.9 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 in vacuo
  7. temperatureThe residue was cooled to 0° C.
  8. additionsaturated Na2CO3 (100 mL) was added
  9. extractionthen was extracted with EtOAc (3×50 mL)
  10. dry with materialThe combined organic layers were dried (Na2SO4)
  11. filtrationfiltered
  12. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-05d345ea226a4fb1832fba6c3f307c4d
Source dataset
uspto-grants-2000_12
Patent number
US06156758

Reaction notes

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