Potassium Carbonate → HCID 59441728, compound

HRID 1014335Notes

Reaction equation

HRID 1014335 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[N+:12]([O-:14])=[O:13])[NH:8][CH2:7][CH2:6]2.Cl[CH2:16][C:17]([N:19]([CH3:21])[CH3:20])=[O:18].C(=O)([O-])[O-].[K+].[K+]>C1COCC1.C(OCC)(=O)C>[CH3:20][N:19]([CH3:21])[C:17](=[O:18])[CH2:16][N:8]1[C:9]2[C:5](=[CH:4][C:3]([O:2][CH3:1])=[C:11]([N+:12]([O-:14])=[O:13])[CH:10]=2)[CH2:6][CH2:7]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 758862-chloro-N,N-dimethylacetamideHCID 594416565-methoxy-6-nitro-2,3-dihydro-1H-indole

Product 1

HCID 59441728HCID 59441728, compoundYield 16%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of 5-(methyloxy)-6-nitro-2,3-dihydro-1H-indole (0.7 g, 3.61 mmol) in THF (100 mL) was added 2-chloro-N,N-dimethylacetamide (1.11 g, 10.8 mmol), and potassium carbonate (2.98 g, 21.6 mmol). After heating at 65° C. for 4 days, the reaction was diluted with ethyl acetate (100 mL) and washed with water (100 mL). The organic layer was separated, adsorbed onto silica gel, and purified by column chromatography (DCM to 2% MeOH/DCM) to provide N,N-dimethyl-2-[5-(methyloxy)-6-nitro-2,3-dihydro-1H-indol-1-yl]acetamide (0.16 g, 16%). ESIMS (M+H)+=280.

Workup

  1. washwashed with water (100 mL)
  2. customThe organic layer was separated
  3. custompurified by column chromatography (DCM to 2% MeOH/DCM)

Sources & evidence

ORD record
ord-181ce5efba5e4da88f187c06c331c785
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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