HCID 67327384, compound → HCID 67328955, compound

HRID 1023352Notes

Reaction equation

HRID 1023352 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([O:10][C:11]2[CH:12]=[C:13]3[C:18](=[CH:19][CH:20]=2)[CH:17]=[C:16]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH:15]=[CH:14]3)=[N:8][CH:9]=1)([O-])=O>CCO.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([O:10][C:11]2[CH:12]=[C:13]3[C:18](=[CH:19][CH:20]=2)[CH:17]=[C:16]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH:15]=[CH:14]3)=[N:8][CH:9]=1

Participants

4

Reactant 1

HCID 67327384HCID 67327384, compound

Product 1

HCID 67328955HCID 67328955, compoundYield 92.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of ethyl 6-[(5-nitropyridin-2-yl)oxy]naphthalene-2-carboxylate (23.3 g) in EtOH (460 mL) was added Pd/C (0.367 g) under a H2 atmosphere. Then the reaction mixture was warmed to 50° C., and stirred for 7.5 hours. The reaction mixture was filtered off on celite, and the filtrate was concentrated under reduced pressure. The residual solid was dried under reduced pressure at 60° C. to afford ethyl 6-[(5-aminopyridin-2-yl)oxy]naphthalene-2-carboxylate as a pale brown powder (19.6 g).

Workup

  1. filtrationThe reaction mixture was filtered off on celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residual solid was dried under reduced pressure at 60° C.

Sources & evidence

ORD record
ord-b3c0b1eb0d8b4f5dbfdef151285496b0
Source dataset
uspto-grants-2014_05
Patent number
US08722663B2

Reaction notes

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