Sodium Hydroxide → Pyrido[2,3-b][1,5]benzoxazepin-5(6H)-one

HRID 1946569Notes

Reaction equation

HRID 1946569 reaction equation
Cl[C:2]1[N:17]=[CH:16][CH:15]=[CH:14][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[OH:13])=[O:5].[OH-].[Na+]>CN(C=O)C>[N:17]1[C:2]2[O:13][C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=3[NH:6][C:4](=[O:5])[C:3]=2[CH:14]=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 1211386HCID 1211386, compound

Product 1

HCID 4296293Pyrido[2,3-b][1,5]benzoxazepin-5(6H)-oneYield 58%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

Title compound 13 (3.65 g, 14.7 mmol) was dissolved in DMF (25.0 mL) and sodium hydroxide (0.706 g, 17.7 mmol) was added. The reaction mixture was stirred at 130° C. for 5 hours. The mixture was cooled down to room temperature and an ice/water mixture was added. The precipitate was filtered then triturated in ethanol to afford title compound 14 (1.798 g, 58%) as a white solid. LRMS (ESI): (calc) 212.06 (found) 213.2 (MH)+.

Workup

  1. temperatureThe mixture was cooled down to room temperature
  2. filtrationThe precipitate was filtered
  3. customthen triturated in ethanol

Sources & evidence

ORD record
ord-7b43523d00224e938690083c2463b935
Source dataset
uspto-grants-2013_03
Patent number
US08399452B2

Reaction notes

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