1,2-Dichloroethane → HCID 22561818, compound

HRID 983028Notes

Reaction equation

HRID 983028 reaction equation
[O:1]=[C:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[C:11]2[CH:12]=[C:13]([CH:17]=[CH:18][CH:19]=2)[C:14](O)=[O:15])[NH:3]1.C1C=CC2N(O)N=[N:26][C:24]=2C=1.C(Cl)CCl.CN>CN(C=O)C>[CH3:24][NH:26][C:14](=[O:15])[C:13]1[CH:17]=[CH:18][CH:19]=[C:11]([C:8]2[CH:7]=[CH:6][CH:5]=[C:4]3[C:9]=2[CH2:10][C:2](=[O:1])[NH:3]3)[CH:12]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 6329MethylamineHCID 757711-HydroxybenzotriazoleHCID 22561961HCID 22561961, compound

Product 1

HCID 22561818HCID 22561818, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-(2-oxo-2,3-dihydro-1H-indol-4-yl)benzoic acid (1.27 g, 5.0 mmol), HOBt (0.68 g, 5.0 mmol) and EDC (1.44 g, 7.5 mmol) in DMF (10 mL) was stirred at room temperature for 30 minutes. To the mixture was added methylamine (2M in THF, 3.75 mL, 7.5 mmol), it was then stirred at room temperature for overnight. Most of the solvent was removed under reduced pressure and the residue was diluted with sat. NaHCO3 (20 mL). The precipitate was collected by filtration, washed with water and dried. The crude product was recrystallized from DCM-hexane to give 1.14 g (86%) of N-methyl-3-(2-oxo-2,3-dihydro-1H-indol-4-yl)-benzamide as a light yellow solid.

Workup

  1. stirringwas then stirred at room temperature for overnight
  2. customMost of the solvent was removed under reduced pressure
  3. additionthe residue was diluted with sat. NaHCO3 (20 mL)
  4. filtrationThe precipitate was collected by filtration
  5. washwashed with water
  6. customdried
  7. customThe crude product was recrystallized from DCM-hexane

Sources & evidence

ORD record
ord-892d4b5dd870472294931463e45a283c
Source dataset
uspto-grants-2005_03
Patent number
US06861418B2

Reaction notes

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