HCID 11799307, compound → HCID 22007341, compound

HRID 1740642Notes

Reaction equation

HRID 1740642 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]2[C:17]3[C:12](=[CH:13][C:14]([O:20]CC4C=CC=CC=4)=[C:15]([O:18][CH3:19])[CH:16]=3)[CH:11]=[C:10](C(OC)=O)[C:9]=2[C:32]([O:34][CH3:35])=[O:33])[CH:5]=[CH:4][N:3]=1>C(O)(=O)C.O1CCOCC1.[C].[Pd]>[Cl:1][C:2]1[CH:7]=[C:6]([CH:8]2[C:17]3[C:12](=[CH:13][C:14]([OH:20])=[C:15]([O:18][CH3:19])[CH:16]=3)[CH:11]=[CH:10][C:9]2([C:32]([O:34][CH3:35])=[O:33])[C:32]([O:34][CH3:35])=[O:33])[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 1

HCID 11799307HCID 11799307, compound

Product 1

HCID 22007341HCID 22007341, compoundYield 123.7%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalyst2×HCID 176Acetic AcidSolvent2×HCID 312751,4-DioxaneSolvent2×

Procedure

To a suspension of 1-(2-chloro-4-pyridyl)-2,3-bis(methoxycarbonyl)-6-benzyloxy-7-methoxynaphthalene (6.6 g) in a mixture of acetic acid and dioxane (1:1, 1000 ml) is added 10% palladium-carbon (2 g), and the mixture is subjected to medium-pressure catalytic hydrogenation at room temperature overnight with using a Parr-reduction apparatus. To the reaction solution is added a mixture of acetic acid and dioxane (1000 ml), and thereto is added 10% palladium-carbon (2 g). The mixture is subjected to medium-pressure catalytic hydrogenation at room temperature for 18 hours with using a Parr-reduction apparatus. The catalyst is removed by filtration, and the filtrate is concentrated under reduced pressure. The residue is crystallized from ethanol to give 1-(2-chloro-4-pyridyl)-2,2-bis(methoxycarbonyl)-6-hydroxy-7-methoxynaphthalene (3.35 g, yield; 62%).

Workup

  1. additionTo the reaction solution is added
  2. waitThe mixture is subjected to medium-pressure catalytic hydrogenation at room temperature for 18 hours
  3. customThe catalyst is removed by filtration
  4. concentrationthe filtrate is concentrated under reduced pressure
  5. customThe residue is crystallized from ethanol

Sources & evidence

ORD record
ord-378fc07e5d8d4a8d8f49e8fc246c1da0
Source dataset
uspto-grants-1999_10
Patent number
US05969140

Reaction notes

Loading…