Ammonium formate → HCID 18943538, compound

HRID 925223Notes

Reaction equation

HRID 925223 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]([N:5]1[CH2:11][CH2:10][C:9]2[CH:12]=[C:13]([N+:16]([O-])=O)[CH:14]=[CH:15][C:8]=2[CH2:7][CH2:6]1)=[O:4].C([O-])=O.[NH4+]>C1COCC1>[NH2:16][C:13]1[CH:14]=[CH:15][C:8]2[CH2:7][CH2:6][N:5]([C:3](=[O:4])[C:2]([F:20])([F:1])[F:19])[CH2:11][CH2:10][C:9]=2[CH:12]=1

Participants

4

Reactant 2

HCID 2723923Ammonium formateHCID 18943563HCID 18943563, compound

Product 1

HCID 18943538HCID 18943538, compoundYield 84.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Into a 500 ml round bottomed flask, the product from step (b) (17 g) and ammonium formate (17 g) in THF (250 ml) were added. To the nitrogen purged reaction mixture, 10% Pd—C (4 g) was added. The reaction mixture was stirred at reflux for 3 hours. The reaction mixture was allowed to cool to room temperature and filtered through celite. The filtrate was diluted with water (200 ml) and extracted with EtOAc (3×). The combined EtOAc extracts were washed with saturated NaHCO3, brine, dried over NaSO4, and solvent evaporated in vacuo to give the sub-title compound as an off-white solid (12.9 g). 1H NMR (300 MHz, DMSO-d6) δ 6.83-6.78 (m, 1H); 6.39-6.31 (m, 2H); 4.91 (s, 2H); 3.66-3.56 (m, 4H); 2.81-2.73 (m, 4H); MS: ESI (positive): 259 (M+H).

Workup

  1. customTo the nitrogen purged
  2. customreaction mixture, 10% Pd—C (4 g)
  3. additionwas added
  4. temperatureat reflux for 3 hours
  5. filtrationfiltered through celite
  6. additionThe filtrate was diluted with water (200 ml)
  7. extractionextracted with EtOAc (3×)
  8. washThe combined EtOAc extracts were washed with saturated NaHCO3, brine
  9. dry with materialdried over NaSO4, and solvent
  10. customevaporated in vacuo

Sources & evidence

ORD record
ord-170c79b15151413a8ff953d5b22a8cf7
Source dataset
uspto-grants-2016_03
Patent number
US09284277B2

Reaction notes

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