N-Methylaniline → 5-chloro-2-[3-(N-methylanilino)propyl]-3-phenylisoindole-1-carboxylic acid ethyl ester

HRID 372334Notes

Reaction equation

HRID 372334 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:22][CH2:23][CH2:24]OS(C)(=O)=O)[C:8]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:9]2[C:14]=1[CH:13]=[CH:12][C:11]([Cl:15])=[CH:10]2)=[O:5])[CH3:2].[CH3:30][NH:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>CN(C)P(=O)(N(C)C)N(C)C>[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:22][CH2:23][CH2:24][N:31]([CH3:30])[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:8]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:9]2[C:14]=1[CH:13]=[CH:12][C:11]([Cl:15])=[CH:10]2)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 7515N-MethylanilineHCID 54315092HCID 54315092, compound

Product 1

HCID 539973495-chloro-2-[3-(N-methylanilino)propyl]-3-phenylisoindole-1-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Procedure

A solution of 4.36 g. of 5-chloro-2-{3-[(methylsulfonyl)oxy]propyl}-3-phenylisoindole-1-carboxylic acid ethyl ester in 25 ml. of hexamethylphosphoric acid triamide is treated with 25 ml. of N-methylaniline and heated at 80° C. for 24 hours. The mixture is then evaporated to dryness under reduced pressure, and the residue treated with 250 ml. of ice-water. The oily precipitate is taken up in methylene chloride and the extract washed with a saturated solution of sodium chloride, dried over sodium sulfate and concentrated to dryness. The resulting oil is purified by chromatography on 150 g. of aluminum oxide [neutral; Brockmann activity I]. By elution with methylene chloride and evaporation of the solvent, there is obtained 5-chloro-2-[3-(N-methylanilino)propyl]-3-phenylisoindole-1-carboxylic acid ethyl ester; melting point 108°-110° C. Crystallization from ether/hexane gives almost colorless crystals of the same melting point.

Workup

  1. customThe mixture is then evaporated to dryness under reduced pressure
  2. additionthe residue treated with 250 ml
  3. washthe extract washed with a saturated solution of sodium chloride
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated to dryness
  6. customThe resulting oil is purified by chromatography on 150 g
  7. washBy elution
  8. customwith methylene chloride and evaporation of the solvent

Sources & evidence

ORD record
ord-3ce753987ec24d5c90b42079b9bd8a14
Source dataset
uspto-grants-1978_05
Patent number
US04090027

Reaction notes

Loading…