Acetic Anhydride → 2,2-Dimethyl-N-[2-(1-acetyl-2,3-dihydro-1H-indol-2-yl)phenyl]propanamide

HRID 249334Notes

Reaction equation

HRID 249334 reaction equation
[CH3:1][C:2]([CH3:22])([CH3:21])[C:3]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH:12]1[CH2:20][C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[NH:13]1)=[O:4].C(N(CC)CC)C.[C:30](OC(=O)C)(=[O:32])[CH3:31]>C(Cl)Cl>[CH3:1][C:2]([CH3:22])([CH3:21])[C:3]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH:12]1[CH2:20][C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]1[C:30](=[O:32])[CH3:31])=[O:4]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 197613982,2-Dimethyl-N-[2-(2,3-dihydro-1H-indol-2-yl)phenyl]propanamide

Product 1

HCID 197614182,2-Dimethyl-N-[2-(1-acetyl-2,3-dihydro-1H-indol-2-yl)phenyl]propanamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an ice cold solution of 3.5 g 2,2-dimethyl-N-[2-(2,3-dihydro-1H-indol-2-yl)phenyl]propanamide in 35 ml CH2Cl2 was added 8.4 ml triethylamine, followed by dropwise addition of 4.2 ml acetic anhydride. The resulting solution was stirred at room temperature for two hours and then quenched with water. The organic layer was washed successively with 5% aq. HCl, water, saturated NaHCO3 and brine, and dried (MgSO4). Concentration, trituration with hexane and recrystallization from toluene/hexane gave 3.1 g solid, m.p. 184°-186° C.

Workup

  1. customquenched with water
  2. washThe organic layer was washed successively with 5% aq. HCl, water, saturated NaHCO3 and brine
  3. dry with materialdried (MgSO4)
  4. concentrationConcentration, trituration
  5. customwith hexane and recrystallization from toluene/hexane

Sources & evidence

ORD record
ord-deb6097530bc4be7952020af4bb7cec4
Source dataset
uspto-grants-1993_05
Patent number
US05214059

Reaction notes

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