HCID 22724355, compound → HCID 22724148, compound

HRID 2086824Notes

Reaction equation

HRID 2086824 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([NH:15][C:16]3[C:21]([N+:22]([O-])=O)=[CH:20][CH:19]=[CH:18][N:17]=3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1>[Pd].C(O)C.O1CCOCC1>[NH2:22][C:21]1[C:16]([NH:15][C:9]2[CH:10]=[CH:11][C:12]([O:13][CH3:14])=[C:7]([O:6][CH:1]3[CH2:2][CH2:3][CH2:4][CH2:5]3)[CH:8]=2)=[N:17][CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 1

HCID 22724355HCID 22724355, compound

Product 1

HCID 22724148HCID 22724148, compoundYield 84%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 2-[(3-cyclopentyloxy-4-methoxyphenyl)-amino]-3-nitropyridine (1.30 g) and 10% palladium on carbon (0.3 g) in ethanol (20 ml) and 1,4-dioxane (20 ml) was stirred under hydrogen (3 atm) at room temperature for 1 hours. The catalyst was removed by filtration and the solvent was evaporated. The resulting solid was collected and washed with isopropyl ether to give 3-amino-2-[(3-cyclopentyloxy-4-methoxyphenyl)amino]pyridine (992 mg).

Workup

  1. customThe catalyst was removed by filtration
  2. customthe solvent was evaporated
  3. customThe resulting solid was collected
  4. washwashed with isopropyl ether

Sources & evidence

ORD record
ord-a4b66dbeddd04149ac315e0662e5b902
Source dataset
uspto-grants-2004_04
Patent number
US06727245B2

Reaction notes

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