Acetic Acid → 5-Amino-6-((S)-2-imidazol-1-yl-1-pyridin-3-yl-ethoxy)-3,4-dihydro-2H-naphthalen-1-one

HRID 496429Notes

Reaction equation

HRID 496429 reaction equation
[N:1]1([CH2:6][C@H:7]([C:23]2[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=2)[O:8][C:9]2[C:10]([N+:20]([O-])=O)=[C:11]3[C:16](=[CH:17][CH:18]=2)[C:15](=[O:19])[CH2:14][CH2:13][CH2:12]3)[CH:5]=[CH:4][N:3]=[CH:2]1.CO.C(O)(=O)C.C([O-])(O)=O.[Na+]>[Fe].CCOC(C)=O.O>[NH2:20][C:10]1[C:9]([O:8][C@@H:7]([C:23]2[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=2)[CH2:6][N:1]2[CH:5]=[CH:4][N:3]=[CH:2]2)=[CH:18][CH:17]=[C:16]2[C:11]=1[CH2:12][CH2:13][CH2:14][C:15]2=[O:19]

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 887MethanolHCID 516892Sodium BicarbonateHCID 697370746-((S)-2-Imidazol-1-yl-1-pyridin-3-yl-ethoxy)-5-nitro-3,4-dihydro-2H-naphthalen-1-one

Product 1

HCID 697352345-Amino-6-((S)-2-imidazol-1-yl-1-pyridin-3-yl-ethoxy)-3,4-dihydro-2H-naphthalen-1-oneYield 46.6%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 6-((S)-2-Imidazol-1-yl-1-pyridin-3-yl-ethoxy)-5-nitro-3,4-dihydro-2H-naphthalen-1-one (1.60 g, 4.23 mmol), MeOH (85 mL), H2O (19 mL) and glacial acetic acid (2.4 mL, 42 mmol) was treated at reflux with iron powder (2.34 g, 42 mmol). The reaction was monitored by mass spectrometry and was complete in 4 h. The volume of solvent was reduced under reduced pressure. EtOAc and dilute aqueous NaHCO3 were added. A brownish-green emulsion formed which was filtered through Celite. The mixture was extracted with EtOAc. The combined organic layer was washed with dilute aqueous NaHCO3 and brine, dried over Na2SO4, and concentrated under reduced pressure to give an off-white foam (0.685 g, 1.97 mmol, 46%). The structure was confirmed by NMR and mass spectrometry. MS m/z 349 (M++H).

Workup

  1. additionwas treated
  2. customA brownish-green emulsion formed which
  3. filtrationwas filtered through Celite
  4. extractionThe mixture was extracted with EtOAc
  5. washThe combined organic layer was washed with dilute aqueous NaHCO3 and brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6e1990f2a90e4710b89d79cebe27b6ce
Source dataset
uspto-grants-2005_09
Patent number
US06943183B2

Reaction notes

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