N,N-Dimethylaniline → HCID 68521888, compound

HRID 1992340Notes

Reaction equation

HRID 1992340 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]#[N:11])=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.CN(C)C1C=CC=CC=1.Cl[CH:22]([CH3:26])[C:23](Cl)=[O:24].C(Cl)[Cl:28]>O>[Cl:28][CH2:26][CH2:22][C:23]([N:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]#[N:11])=[CH:7][CH:8]=2)[CH2:3][CH2:2]1)=[O:24]

Participants

6

Reactant 4

HCID 949N,N-DimethylanilineHCID 6344DichloromethaneHCID 1110192-Chloropropionyl chlorideHCID 219076392,3-Dihydro-1H-indole-5-carbonitrile

Product 1

HCID 68521888HCID 68521888, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 2,3-dihydro-1H-indole-5-carbonitrile (8 g, 0.0556 mol; see step (iv) above) in DCM (50 mL) at 0° C. was added N,N-dimethylaniline (13.5 g, 0.1112 mol) followed by 2-chloropropionyl chloride (8.46 g, 0.0667 mol). The reaction mixture was stirred for 3 h before being diluted with water and extracted with DCM. The organic layer was washed with water and brine, dried over sodium sulfate and then concentrated under reduced pressure. The resulting residue was purified by column chromatography over silica gel to yield the sub-title compound as a pale yellow solid. Yield: 10.5 g.

Workup

  1. extractionextracted with DCM
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by column chromatography over silica gel

Sources & evidence

ORD record
ord-0243932a2ad34898aee85f4c785f8a47
Source dataset
uspto-grants-2010_01
Patent number
US07648985B2

Reaction notes

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