Sodium Hydroxide → HCID 20464758, compound

HRID 325427Notes

Reaction equation

HRID 325427 reaction equation
[CH3:1][N:2]1[C:6]([CH2:7][C:8]([O:10]C)=[O:9])=[CH:5][C:4]2[CH:12]([CH3:22])[CH2:13][C:14]3[CH:21]=[CH:20][CH:19]=[CH:18][C:15]=3[C:16](=[O:17])[C:3]1=2.[OH-].[Na+]>C(O)C.O>[CH3:1][N:2]1[C:6]([CH2:7][C:8]([OH:10])=[O:9])=[CH:5][C:4]2[CH:12]([CH3:22])[CH2:13][C:14]3[CH:21]=[CH:20][CH:19]=[CH:18][C:15]=3[C:16](=[O:17])[C:3]1=2

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 20464792HCID 20464792, compound

Product 1

HCID 20464758HCID 20464758, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

To a suspension of methyl 5,10-dihydro-1,4-dimethyl-10-oxo-4H-benzo-[5,6]-cyclohepta[1,2-b]pyrrol-2-acetate (26 mg, 0.087 mmoles) in a mixture of 4 cc ethanol and 0.5 cc water, slight ice-bath cooling, is added 0.06 cc of 2.5 N sodium hydroxide solution. After stirring overnight (nitrogen atmosphere) at ambient temperatures, water (4 cc) is added, the ethanol removed in vacuo, the mixture filtered, and the filtrate acidified with 2 N hydrochloric acid. After aging, the supernatent aqueous solution is decanted from the yellow oil that forms, and the oil washed well with water. The oil is then dissolved in ether, the ether solution dried and concentrated to 20.3 mg (83%) of 5,10-dihydro-1,4-dimethyl-10-oxo-4H-benzo[5,6]cyclohepta[1,2-b]pyrrol-2-yl-acetic acid as a yellow oil.

Workup

  1. temperaturecooling
  2. additionis added
  3. customthe ethanol removed in vacuo
  4. filtrationthe mixture filtered
  5. customthe supernatent aqueous solution is decanted from the yellow oil that forms
  6. washthe oil washed well with water
  7. dissolutionThe oil is then dissolved in ether
  8. dry with materialthe ether solution dried
  9. concentrationconcentrated to 20.3 mg (83%) of 5,10-dihydro-1,4-dimethyl-10-oxo-4H-benzo[5,6]cyclohepta[1,2-b]pyrrol-2-yl-acetic acid as a yellow oil

Sources & evidence

ORD record
ord-3db038fc450640849b4c170edd91181b
Source dataset
uspto-grants-1984_04
Patent number
US04440779

Reaction notes

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