Sodium Hydroxide → HCID 18695633, compound

HRID 1920658Notes

Reaction equation

HRID 1920658 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([NH2:15])[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:16](Cl)(=[O:23])[C:17]1[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=1.[OH-].[Na+]>C(Cl)Cl.O>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([NH:15][C:16](=[O:23])[C:17]3[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 417436Pyridine-4-carbonyl chlorideHCID 27793343-(Cyclopentyloxy)-4-methoxyaniline

Product 1

HCID 18695633HCID 18695633, compoundYield 68.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

7.0 g (33.8 mmol) of 3-cyclopentyloxy-4-methoxy-phenylamine (Garcia et al., JOC, 2005, 70, p 1050) were dissolved in 150 ml of DCM. The solution was cooled to 0° C. and 5.74 g (40.5 mmol) isonicotinoyl chloride in 50 ml DCM were added to the solution. A precipitate was formed. The reaction mixture was subsequently stirred at room temperature during two hours. A solution of 2.7 g NaOH in 100 ml water was added to the reddish reaction mixture. The organic layer was separated, dried over Na2SO4 and evaporated. The crude product was purified by flash chromatography on silica gel (ethyl acetate/n-hexane 2:1) to afford 7.2 g (62%) of the desired product. MS (ESI): 313.1.

Workup

  1. customA precipitate was formed
  2. customThe organic layer was separated
  3. dry with materialdried over Na2SO4
  4. customevaporated
  5. customThe crude product was purified by flash chromatography on silica gel (ethyl acetate/n-hexane 2:1)

Sources & evidence

ORD record
ord-86b6118f72864e17a4e99f5f0b742c8b
Source dataset
uspto-grants-2012_05
Patent number
US08173609B2

Reaction notes

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