Hydrochloric Acid → HCID 13325935, compound

HRID 325413Notes

Reaction equation

HRID 325413 reaction equation
[CH3:1][N:2]1[C:6]([CH2:7][C:8]([O:10]CC)=[O:9])=[CH:5][C:4]2[O:13][CH2:14][C:15]3[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=3[C:17](=[O:18])[C:3]1=2.[OH-].[Na+].Cl>C(O)C.O>[CH3:1][N:2]1[C:6]([CH2:7][C:8]([OH:10])=[O:9])=[CH:5][C:4]2[O:13][CH2:14][C:15]3[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=3[C:17](=[O:18])[C:3]1=2

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 20464751HCID 20464751, compound

Product 1

HCID 13325935HCID 13325935, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Ethyl 5,10-dihydro-1-methyl-10-oxo-1H-[2]benzoxepino[4,3-b]pyrrole-2-acetate (196 mg, 0.66 mmol) is dissolved in ethanol and 2.5 N aqueous sodium hydroxide (2 ml, 5 mmol) is added dropwise at reflux under nitrogen. The reaction is heated for an additional ten minutes, then the solution is cooled and diluted with water (5 ml). The resulting mixture is acidified with 2.5 N aqueous HCl (3 ml). The product separates as an oil, then solidifies on scratching. The solid is filtered, washed with water and dried to give 160 ml crude product. The product is recrystallized from ethanol to give 102 mg of 5,10-dihydro-1-methyl-10-oxo-1H-[2]benzoxepino[4,3-b]pyrrole-2-acetic acid, M.P. 114°-116° (dec).

Workup

  1. temperatureat reflux under nitrogen
  2. temperatureThe reaction is heated for an additional ten minutes
  3. temperaturethe solution is cooled
  4. filtrationThe solid is filtered
  5. washwashed with water
  6. customdried
  7. customto give 160 ml crude product
  8. customThe product is recrystallized from ethanol

Sources & evidence

ORD record
ord-1a461099cd4e442d910bb1d3fddbaf02
Source dataset
uspto-grants-1984_04
Patent number
US04440779

Reaction notes

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