Potassium Hydroxide → HCID 178526709, compound

HRID 1890282Notes

Reaction equation

HRID 1890282 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][CH:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[C:5]([N+:15]([O-:17])=[O:16])=[CH:4][CH:3]=1.[OH-:18].[K+]>O1CCOCC1>[N+:15]([C:5]1[CH:4]=[CH:3][C:2]([OH:18])=[N:7][C:6]=1[NH:8][CH:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1)([O-:17])=[O:16]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 43610512HCID 43610512, compound

Product 1

HCID 178526709HCID 178526709, compoundYield 98.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

6-Chloro-3-nitro-N-(tetrahydro-2H-pyran-4-yl)pyridin-2-amine (0.186 g, 0.722 mmol), 1 M aqueous potassium hydroxide solution (8.0 mL, 16.0 mmol) and dioxane (20 mL) were heated to 100° C. for 4 h. After cooling, the pH was adjusted to ˜7 and the mixture was extracted with EtOAc. The EtOAc extract was concentrated under reduced pressure to give the title compound (0.170 g). LCMS m/z=240.3 [M+H]+; 1H NMR (400 MHz, methanol-d4) δ ppm 1.65-1.80 (m, 2H), 2.05-2.15 (m, 2H), 3.60-3.70 (m, 2H), 4.00-4.10 (m, 2H), 4.20-4.30 (m, 1H), 5.92 (d, J=9.8 Hz, 1H), 8.32 (d, J=9.8 Hz, 1H).

Workup

  1. temperatureAfter cooling
  2. extractionthe mixture was extracted with EtOAc
  3. extractionThe EtOAc extract
  4. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-3dd7edf10660472a9782d47c9fe4a6ed
Source dataset
uspto-grants-2013_08
Patent number
US08507473B2

Reaction notes

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