4-Isopropylaniline → HCID 57429432, compound

HRID 1640022Notes

Reaction equation

HRID 1640022 reaction equation
Br[CH2:2][C:3]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][C:4]=1[C:5]([O:7]CC)=O.[CH:15]([C:18]1[CH:24]=[CH:23][C:21]([NH2:22])=[CH:20][CH:19]=1)([CH3:17])[CH3:16].[O-]CC.[Na+]>C(O)C>[Cl:14][C:11]1[CH:10]=[C:4]2[C:3]([CH2:2][N:22]([C:21]3[CH:23]=[CH:24][C:18]([CH:15]([CH3:17])[CH3:16])=[CH:19][CH:20]=3)[C:5]2=[O:7])=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 74644-IsopropylanilineHCID 2723922Sodium ethoxideHCID 13272463Ethyl 2-(bromomethyl)-5-chlorobenzoate

Product 1

HCID 57429432HCID 57429432, compoundYield 53.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl 2-(bromomethyl)-5-chlorobenzoate (0.553 g, 1.99 mmol), 4-isopropylaniline (0.269 g, 1.99 mmol) and sodium ethoxide (0.406 g, 5.97 mmol) in ethanol (40 mL) was heated at reflux overnight. After this time, the mixture was cooled to room temperature and concentrated under vacuum. The mixture was partitioned between 1 N HCl and ethyl acetate. The organic layer was separated, washed with 1 N HCl, then with 1:1 water/brine solution, dried over sodium sulfate and filtered. Concentration under vacuum and recrystallization from ethyl acetate afforded 6-chloro-2-(4-isopropylphenyl)isoindolin-1-one (0.302 g, 53%) as an off-white solid: m.p. 206-209° C.; 1H NMR (500 MHz, CDCl3) δ 7.89 (d, J=1.9 Hz, 1H), 7.73 (dt, J=8.6, 2.7 Hz, 2H), 7.55 (dd, J=8.1, 1.9 Hz, 1H), 7.45 (d, J=8.0 Hz, 1H), 7.30 (dt, J=8.5, 2.5 Hz, 2H), 4.83 (s, 2H), 2.96-2.90 (m, 1H), 1.26 (d, 6H); ESI MS m/z 286 [M+H]+.

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. concentrationconcentrated under vacuum
  4. customThe mixture was partitioned between 1 N HCl and ethyl acetate
  5. customThe organic layer was separated
  6. washwashed with 1 N HCl
  7. dry with materialwith 1:1 water/brine solution, dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationConcentration
  10. customunder vacuum and recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-18922b1730304cbba908a1f6ff1e29cc
Source dataset
uspto-grants-2012_02
Patent number
US08110681B2

Reaction notes

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