Sodium Hydroxide → 1071432-28-4

HRID 1662048Notes

Reaction equation

HRID 1662048 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]([O:13][CH3:14])=[O:12])[CH:9]=2)[CH:4]=[CH:3]1.[Na].[OH-].[Na+]>C(O)(=O)C>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]([O:13][CH3:14])=[O:12])[CH:9]=2)[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 639843Methyl N-methylindole-6-carboxylateHCID 5360545Sodium

Product 1

HCID 594540311071432-28-4Yield 59.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a mixture of methyl N-methylindole-6-carboxylate (1.5 g) and acetic acid (22.5 ml) was added sodium cyanoboride (1.62 g), followed by stirring at room temperature for 1 hour. The reaction mixture was poured into ice-water (100 ml), and sodium hydroxide (pellet) was added thereto to adjust the pH to about 10, followed by extraction with ethyl acetate (60 ml). The organic layer was washed with a saturated sodium bicarbonate solution three times, and saturated brine in this order, and dried over anhydrous magnesium sulfate, and the solvent was then removed by evaporation under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1) to obtain methyl N-methylindoline-6-carboxylate (900 mg) as a pale yellow oily substance.

Workup

  1. additionwas added
  2. extractionfollowed by extraction with ethyl acetate (60 ml)
  3. washThe organic layer was washed with a saturated sodium bicarbonate solution three times, and saturated brine in this order
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was then removed by evaporation under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-5b7f1cdbea8949cc8f526bc91ebfa2dd
Source dataset
uspto-grants-2011_10
Patent number
US08030489B2

Reaction notes

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