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

HRID 718099Notes

Reaction equation

HRID 718099 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-e3aebc5f4c9a41399eada6980df42006
Source dataset
uspto-grants-2015_11
Patent number
US09193749B2

Reaction notes

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