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

HRID 1946629Notes

Reaction equation

HRID 1946629 reaction equation
ONC(=O)C1C=CC(OCC[N:13]2[C:19](=[O:20])[C:18]3[CH:21]=[CH:22][CH:23]=[N:24][C:17]=3[O:16][C:15]3[CH:25]=[CH:26][CH:27]=[CH:28][C:14]2=3)=CC=1.[OH-].[Na+].O>CN(C=O)C>[N:24]1[C:17]2[O:16][C:15]3[CH:25]=[CH:26][CH:27]=[CH:28][C:14]=3[NH:13][C:19](=[O:20])[C:18]=2[CH:21]=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 59783469HCID 59783469, 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 430 (3.65 g, 14.7 mmol) was dissolved in DMF (25.0 mL) and sodium hydroxide powder (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 ice cooled water was added. The precipitate was filtered. The solid was triturated in ethanol to afford title compound 431 (1.798 g, 58%) as a white solid. 1H NMR (DMSO-d6) δ (ppm): 10.75 (s, 1H), 8.50 (dd, J=4.8, 2.1 Hz, 1H), 8.27 (dd, J=7.6, 2.0 Hz, 1H), 7.46 (dd, J=7.5, 4.8 Hz, 1H), 7.34 (dd, J=7.8, 1.2 Hz, 1H), 7.25-7.14 (m, 3H). MS (m/z): 213.2 (M+H).

Workup

  1. temperatureThe mixture was cooled down to room temperature
  2. additionwas added
  3. filtrationThe precipitate was filtered
  4. customThe solid was triturated in ethanol

Sources & evidence

ORD record
ord-72c53a9c24dd46e0ad41eb17d764b955
Source dataset
uspto-grants-2013_03
Patent number
US08399452B2

Reaction notes

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