Acetic Acid → 9-Chloro-5-hydroxy-3-methyl-7-phenyl-5H-pyrimido[4,5-d][2]benzazepin-1(2H)-one

HRID 464590Notes

Reaction equation

HRID 464590 reaction equation
C([O:4][CH:5]1[C:11]2[N:12]=[C:13]([CH3:17])[NH:14][C:15](=[O:16])[C:10]=2[C:9]2[CH:18]=[CH:19][C:20]([Cl:22])=[CH:21][C:8]=2[C:7]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[N:6]1)(=O)C.[OH-].[Na+].C(O)(=O)C>CCOCC>[Cl:22][C:20]1[CH:19]=[CH:18][C:9]2[C:10]3[C:15](=[O:16])[NH:14][C:13]([CH3:17])=[N:12][C:11]=3[CH:5]([OH:4])[N:6]=[C:7]([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:8]=2[CH:21]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium Hydroxide2×HCID 1357590635-(Acetyloxy)-9-chloro-3-methyl-7-phenyl-5H-pyrimido[4,5-d][2]benzazepin-1(2H)-one

Product 1

HCID 1357590649-Chloro-5-hydroxy-3-methyl-7-phenyl-5H-pyrimido[4,5-d][2]benzazepin-1(2H)-one

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 2.1 g (5.3 mmol) of 5-(acetyloxy)-9-chloro-3-methyl-7-phenyl-5H-pyrimido[4,5-d][2]benzazepin-1(2H)-one and 50 mL of 3N sodium hydroxide was heated on a steam bath for 5 min. The reaction mixture was diluted with 200 mL of ice water and 50 mL of ether. The sodium hydroxide was neutralized with acetic acid and the resulting mixture stirred at room temperature for 30 min. The resulting precipitate was collected by filtration to give an off-white solid. Recrystallization from tetrahydrofuran gave the product as colorless crystals, mp 253°-255° (dec.).

Workup

  1. temperaturewas heated on a steam bath for 5 min
  2. filtrationThe resulting precipitate was collected by filtration
  3. customto give an off-white solid
  4. customRecrystallization from tetrahydrofuran

Sources & evidence

ORD record
ord-6472c943a8e14198802cb7102e43e205
Source dataset
uspto-grants-1985_10
Patent number
US04548750

Reaction notes

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