1,2-Dichloroethane → HCID 22249396, compound

HRID 238453Notes

Reaction equation

HRID 238453 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-5dc2a343525d4c55aeec3a8e27802c4a
Source dataset
uspto-grants-2014_02
Patent number
US08642624B2

Reaction notes

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