Dimethylformamide → Methyl 1-methyl-7-oxo-4,5,6,7-tetrahydro-1H-indole-3-carboxylate

HRID 872191Notes

Reaction equation

HRID 872191 reaction equation
[O:1]=[C:2]1[C:10]2[NH:9][CH:8]=[C:7]([C:11]([O:13][CH3:14])=[O:12])[C:6]=2[CH2:5][CH2:4][CH2:3]1.[CH3:15]N(C=O)C.CI>O>[CH3:15][N:9]1[C:10]2[C:2](=[O:1])[CH2:3][CH2:4][CH2:5][C:6]=2[C:7]([C:11]([O:13][CH3:14])=[O:12])=[CH:8]1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 68276513Methyl 7-oxo-4,5,6,7-tetrahydro-1H-indole-3-carboxylate

Product 1

HCID 68276330Methyl 1-methyl-7-oxo-4,5,6,7-tetrahydro-1H-indole-3-carboxylateYield 95%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of methyl 7-oxo-4,5,6,7-tetrahydro-1H-indole-3-carboxylate (300 mg, 1.55 mmol) in dry DMF (5 mL) K2CO3 (429 mg, 3.10 mmol) and methyl iodide (0.193 mL, 3.10 mmol) were added. The reaction was stirred at room temperature for 3 h, then H2O was added (100 mL) and the product extracted with DCM (3×30 mL). The organic fractions were dried over Na2SO4, filtered, and concentrated in vacuo to give 305 mg (yield: 95%) as light yellow solid.

Workup

  1. extractionthe product extracted with DCM (3×30 mL)
  2. dry with materialThe organic fractions were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto give 305 mg (yield: 95%) as light yellow solid

Sources & evidence

ORD record
ord-f888e2566ef245069022b7f26a36dbec
Source dataset
uspto-grants-2015_03
Patent number
US08975267B2

Reaction notes

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