Sodium Hydroxide → HCID 136165693, compound

HRID 2296326Notes

Reaction equation

HRID 2296326 reaction equation
COC([N:5]1[CH:14]=[C:13]2[C:7]([CH:8]([O:27][C:28](=O)C)[N:9]=[C:10]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[Cl:26])[C:11]3[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:12]=32)=[CH:6]1)=O.[OH-].[Na+]>O1CCCC1.CO.O>[Cl:19][C:17]1[CH:16]=[CH:15][C:12]2[C:13]3[C:7](=[CH:6][NH:5][CH:14]=3)[CH:8]([O:27][CH3:28])[N:9]=[C:10]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[Cl:26])[C:11]=2[CH:18]=1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 13067126HCID 13067126, compound

Product 1

HCID 136165693HCID 136165693, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1.0 g (2.2 mmol) of 4-(acetyloxy)-8-chloro-6-(2-chlorophenyl)-2H,4H-pyrrolo[3,4-d][2]benzazepine-2-carboxylic acid methyl ester and 2.5 ml of 3 N aqueous sodium hydroxide solution in a mixture of 25 ml of tetrahydrofuran and 10 ml of methanol was stirred at 0° for 30 min. The mixture was diluted with water and extracted with methylene chloride. The methylene chloride solution was washed with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate and concentrated at reduced pressure to dryness. The residue was triturated with a mixture of ether and methylene chloride to give a cream colored solid, mp 215°-218°. Recrystallization from a mixture of tetrahydrofuran and hexane gave tan prisms, mp 221°-224°.

Workup

  1. extractionextracted with methylene chloride
  2. washThe methylene chloride solution was washed with saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated at reduced pressure to dryness
  5. customThe residue was triturated with a mixture of ether and methylene chloride
  6. customto give a cream colored solid, mp 215°-218°
  7. customRecrystallization
  8. additionfrom a mixture of tetrahydrofuran and hexane
  9. customgave tan prisms, mp 221°-224°

Sources & evidence

ORD record
ord-e05f1651ea004020a07b0f9b92067ded
Source dataset
uspto-grants-1984_01
Patent number
US04428879

Reaction notes

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