Sodium Hydroxide → HCID 70608306, compound

HRID 426763Notes

Reaction equation

HRID 426763 reaction equation
I.[CH2:2]([N:9]1[CH2:17][CH:16]2[C:11](=[C:12]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:13]3[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:14]=3[CH2:15]2)[CH2:10]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[OH-].[Na+]>C(O)(=O)C>[CH2:2]([N:9]1[CH2:17][CH:16]2[CH:11]([CH:12]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:13]3[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:14]=3[CH2:15]2)[CH2:10]1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24841Hydrogen iodideHCID 70608394HCID 70608394, compound

Product 1

HCID 70608306HCID 70608306, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

190 cc of 57% hydriodic acid are added dropwise to a suspension of 30 g of (9aRS)-2-benzyl-6-chloro-9,9a-dihydro-4-phenyl-benz[f]isoindoline and 46.8 g of red phosphorus in 400 cc of glacial acetic acid, the mixture is subsequently heated to 110° for 5 1/2 hours, is then poured on ice and made alkaline with caustic soda solution. After extraction with ethyl acetate, the organic phase is filtered through Celite, the filtrate is dried and concentrated by evaporation, whereby the title compound, having a M.P. of 115-117° (after crystallization from pentane), is obtained.

Workup

  1. temperaturethe mixture is subsequently heated to 110° for 5 1/2 hours
  2. additionis then poured on ice
  3. extractionAfter extraction with ethyl acetate
  4. filtrationthe organic phase is filtered through Celite
  5. customthe filtrate is dried
  6. concentrationconcentrated by evaporation, whereby the title compound
  7. customa M.P. of 115-117° (after crystallization from pentane)
  8. customis obtained

Sources & evidence

ORD record
ord-b2a11d3345594dc486964dd0307ceb73
Source dataset
uspto-grants-1979_10
Patent number
US04171369

Reaction notes

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