4,7-dihydro-4,7-dioxo-1-(2-propynyl)-6-(2-propynyloxy)-1H-cyclohepta[b]pyridine-2-carboxylic Acid ethyl ester → HCID 53707130, compound

HRID 66147Notes

Reaction equation

HRID 66147 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:11]([CH2:12][C:13]#[CH:14])[C:10]2[CH:15]=[CH:16][C:17](=[O:24])[C:18]([O:20][CH2:21][C:22]#[CH:23])=[CH:19][C:9]=2[C:8](=[O:25])[CH:7]=1)=[O:5])[CH3:2].[H][H]>[Pd].C(O)(=O)C>[CH2:1]([O:3][C:4]([C:6]1[N:11]([CH2:12][CH2:13][CH3:14])[C:10]2[CH:15]=[CH:16][C:17](=[O:24])[C:18]([O:20][CH2:21][CH2:22][CH3:23])=[CH:19][C:9]=2[C:8](=[O:25])[CH:7]=1)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 544541564,7-dihydro-4,7-dioxo-1-(2-propynyl)-6-(2-propynyloxy)-1H-cyclohepta[b]pyridine-2-carboxylic Acid ethyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 53707130HCID 53707130, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 4,7-dihydro-4,7-dioxo-1-(2-propynyl)-6-(2-propynyloxy)-1H-cyclohepta[b]pyridine-2-carboxylic acid ethyl ester (20 g, described in Example 20), 5% palladium on charcoal (2.0 g) and acetic acid (400 ml) is stirred rapidly under an atmosphere of hydrogen until 5.7 liters of hydrogen are absorbed. The mixture is filtered and the filtrate is evaporated. The residue is subjected to chromatography on silica gel using acetone-hexane (1:1). The eluates are evaporated to give a residue of the title compound.

Workup

  1. customare absorbed
  2. filtrationThe mixture is filtered
  3. customthe filtrate is evaporated
  4. customThe eluates are evaporated

Sources & evidence

ORD record
ord-a9d8d5c7c1394be18af0176ae4a3c433
Source dataset
uspto-grants-1978_12
Patent number
US04130649

Reaction notes

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