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

HRID 2295985Notes

Reaction equation

HRID 2295985 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 3 N 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-fcd1c73defb94dd9855d033d335908c5
Source dataset
uspto-grants-1984_01
Patent number
US04427589

Reaction notes

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