Sodium Hydroxide → HCID 20395303, compound

HRID 261205Notes

Reaction equation

HRID 261205 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][CH:7]2[CH2:11][N:10]([CH3:12])[CH2:9][CH:8]2[C:13]#N)=[CH:4][CH:3]=1.[OH-:17].[Na+]>O>[Cl:1][C:2]1[CH:16]=[CH:15][C:5]2[CH2:6][CH:7]3[CH:8]([C:13](=[O:17])[C:4]=2[CH:3]=1)[CH2:9][N:10]([CH3:12])[CH2:11]3

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 20395314HCID 20395314, compound

Product 1

HCID 20395303HCID 20395303, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

25 ml of water are added dropwise to 500 g of polyphosphoric acid at 50° followed by 50 g of 4-(p-chlorobenzyl)-1-methyl-pyrrolidin-3-carbonitrile and the mixture stirred for 1 hour at 125° and then for 21/2 hours at 160°. Ice and 1 liter of 50% sodium hydroxide are added to the cooled mixture which is then extracted with ethyl acetate. The organic phase is washed with water, dried over sodium sulphate and evaporated to yield 6-chloro-3a,4,9,9a-tetrahydro-2-methylbenz[f]isoindolin-4-one. M.P. 148°-150° (hydrogen maleate form).

Workup

  1. custom2 hours
  2. customat 160°
  3. extractionis then extracted with ethyl acetate
  4. washThe organic phase is washed with water
  5. dry with materialdried over sodium sulphate
  6. customevaporated

Sources & evidence

ORD record
ord-30a04b66a2db42a3836c4dedfe7c5b7b
Source dataset
uspto-grants-1979_08
Patent number
US04164583

Reaction notes

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