1,2-Dichloroethane → HCID 22249396, compound

HRID 889946Notes

Reaction equation

HRID 889946 reaction equation
[CH3:1][C:2]1([CH3:14])[C:10]2[C:5](=[CH:6][C:7]([N+:11]([O-:13])=[O:12])=[CH:8][CH:9]=2)[NH:4][CH2:3]1.C1[CH:20]=[N:19][C:18]2N(O)N=NC=2C=1.[CH2:25](Cl)[CH2:26]Cl.CN(C=[O:33])C>C(Cl)Cl>[CH3:18][N:19]([CH3:20])[CH2:25][C:26]([N:4]1[C:5]2[C:10](=[CH:9][CH:8]=[C:7]([N+:11]([O-:13])=[O:12])[CH:6]=2)[C:2]([CH3:14])([CH3:1])[CH2:3]1)=[O:33]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 6228DimethylformamideHCID 181649HOAtHCID 219594663,3-Dimethyl-6-nitroindoline

Product 1

HCID 22249396HCID 22249396, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3,3-Dimethyl-6-nitro-2,3-dihydro-1H-indole (5 g) was dissolved in DMF (100 ml) and HOAt (3.89 g) dimethylamino-acetic acid (5.83 g) and EDC (3.89 g) were added. The reaction was stirred overnight. The mixture was diluted with CH2Cl2 (1 L) and washed with sat'd NaHCO3 (3×200 ml). The organic layer was washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography (SiO2, EtOAc to 5%MeOH/EtOAc) to afford the title compound.

Workup

  1. washwashed with sat'd NaHCO3 (3×200 ml)
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography (SiO2, EtOAc to 5%MeOH/EtOAc)

Sources & evidence

ORD record
ord-ffac32a1b908495fbb69b31742a622d8
Source dataset
uspto-grants-2006_02
Patent number
US06995162B2

Reaction notes

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