Hydrochloric Acid → HCID 19095936, compound

HRID 486776Notes

Reaction equation

HRID 486776 reaction equation
[CH2:1]1[C:5]2=[CH:6][C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=3[N:4]2[CH2:3][C:2]21[CH2:16][C:15](=[O:17])[NH:14][C:13]2=[O:18].[H-].[Na+].I[CH3:22].Cl>CN(C=O)C.O>[CH3:22][N:14]1[C:15](=[O:17])[CH2:16][C:2]2([CH2:3][N:4]3[C:12]4[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=4[CH:6]=[C:5]3[CH2:1]2)[C:13]1=[O:18]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 19095917HCID 19095917, compound

Product 1

HCID 19095936HCID 19095936, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

A solution of 1.96 g of 1',3'-dihydrospiro[pyrrolidine-3,2'-pyrrolo[1,2-a]indole]-2,5-dione [prepared as described in Example 11(iv)] in 10 ml of DMF was added dropwise to a stirred suspension of 330 mg of a 60% dispersion of sodium hydride in mineral oil in 10 ml of DMF. The mixture was treated with 1 ml of iodomethane and stirred for 17 hours. The mixture was diluted with water, neutralized with 1M aqueous hydrochloric acid and extracted with ethyl acetate. The extracts were washed with sodium chloride solution, dried and the solvent was removed by evaporation. Crystallization of the residue from ethyl acetate/n-hexane gave 1.81 g of 1',3'-dihydro-1-methylspiro-[pyrrolidine-3,2'-pyrrolo[1,2-a]indole]-2,5-dione of melting point 154°-156° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extracts were washed with sodium chloride solution
  3. customdried
  4. customthe solvent was removed by evaporation
  5. customCrystallization of the residue from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-fda74564c5b34a548e43e2c2f14e8915
Source dataset
uspto-grants-1994_03
Patent number
US05292747

Reaction notes

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