Potassium Hydroxide → HCID 178526704, compound

HRID 1890348Notes

Reaction equation

HRID 1890348 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[C:5]([N+:15]([O-:17])=[O:16])=[CH:4][CH:3]=1.[OH-:18].[K+]>O1CCOCC1>[CH:9]1([NH:8][C:6]2[N:7]=[C:2]([OH:18])[CH:3]=[CH:4][C:5]=2[N+:15]([O-:17])=[O:16])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 431526936-chloro-N-cyclohexyl-3-nitropyridin-2-amine

Product 1

HCID 178526704HCID 178526704, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 6-chloro-N-cyclohexyl-3-nitropyridin-2-amine (2.16 g, 8.45 mmol) dissolved in dioxane (845 mL) was added 3 M aqueous potassium hydroxide (8.5 mL). The reaction mixture was heated at 100° C. until LCMS showed the starting material was entirely consumed. The reaction mixture was cooled to room temperature and then diluted with water. 1 N HCl was added until the solution turned acidic and a solid was formed. The solid was filtered, washed with water, and dried under vacuum to afford the title compound as a yellow solid (1.58 g). LCMS m/z=238.30 [M+H]+.

Workup

  1. customwas entirely consumed
  2. temperatureThe reaction mixture was cooled to room temperature
  3. additiondiluted with water
  4. addition1 N HCl was added until the solution
  5. customa solid was formed
  6. filtrationThe solid was filtered
  7. washwashed with water
  8. customdried under vacuum

Sources & evidence

ORD record
ord-e7766a7b62d243d79a0e23e1e1961adc
Source dataset
uspto-grants-2013_08
Patent number
US08507473B2

Reaction notes

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