Ammonium formate → HCID 10804962, compound

HRID 357258Notes

Reaction equation

HRID 357258 reaction equation
[O:1]=[C:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH2:6][O:5][C:4]2[CH:13]=[CH:14][C:15]([CH2:17][CH2:18][N:19]([O:23]CC3C=CC=CC=3)[C:20](=[O:22])[CH3:21])=[CH:16][C:3]1=2.C([O-])=O.[NH4+]>C(O)C.[Pd]>[O:1]=[C:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH2:6][O:5][C:4]2[CH:13]=[CH:14][C:15]([CH2:17][CH2:18][N:19]([OH:23])[C:20](=[O:22])[CH3:21])=[CH:16][C:3]1=2

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 10763576HCID 10763576, compound

Product 1

HCID 10804962HCID 10804962, compoundYield 41.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of N-[2-(6,11-dihydro-11-oxodibenz[b,e]oxepin-2-yl)ethyl]-N-(phenylmethoxy)acetamide (4.07 g) in absolute ethanol was treated with ammonium formate (3.2 g) and 700 mg 5% palladium on carbon. The mixture was stirred at room temperature for 1.5 hours then filtered through a short pad of celite. The filtrate was evaporated and the residue purified by flash chromatography (silica gel, 2:1 ethyl acetate-hexane) to give an oil. This oil crystallized from ethyl acetate-hexane to give 1.3 g of N-[2-(6,11-dihydro-11-oxodibenz[b,e]oxepin-2-yl)ethyl]-N-hydroxyacetamide, as crystals, m.p. 113°-115° C.

Workup

  1. filtrationthen filtered through a short pad of celite
  2. customThe filtrate was evaporated
  3. customthe residue purified by flash chromatography (silica gel, 2:1 ethyl acetate-hexane)
  4. customto give an oil
  5. customThis oil crystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-76a014975bfd4a549151d7fdf2d48ce7
Source dataset
uspto-grants-1998_11
Patent number
US05840749

Reaction notes

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