Water → 3-Methylindoline

HRID 1510462Notes

Reaction equation

HRID 1510462 reaction equation
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:3]([CH3:4])=[CH:2]1.C([BH3-])#N.[Na+].O>C(O)(=O)C>[CH3:4][CH:3]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[NH:1][CH2:2]1

Participants

5

Reactant 3

HCID 962WaterHCID 6736SkatoleHCID 5003444Sodium cyanoborohydride

Product 1

HCID 5245043-Methylindoline

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
15 °C

Procedure

Skatole (26.5 g, 202 mmol) was dissolved in acetic acid (500 mL) and cooled to 15° C. Sodium cyanoborohydride (40 g, 637 mmol) was added in portions to this cooled solution. After the addition was complete, stirring was continued for 1 h at RT. Subsequently, water (100 mL) was added and after 15 min at RT, the mixture was evaporated under reduced pressure at 60° C. To the residue was added 0.5 L 5% aq. NaHCO3 and 0.5 L TBME and the organic layer was washed with 5% aq. NaHCO3 (2×250 mL), water (0.5 L), 1M aq. NaOH (100 mL), 5% aq. NaHCO3 (250 mL), and brine (250 mL). After drying over Na2SO4 and filtration, the solvent was removed by evaporation under reduced pressure. Yield: 23.3 g (87%).

Workup

  1. additionAfter the addition
  2. customthe mixture was evaporated under reduced pressure at 60° C
  3. additionTo the residue was added 0.5 L 5% aq. NaHCO3 and 0.5 L TBME
  4. washthe organic layer was washed with 5% aq. NaHCO3 (2×250 mL), water (0.5 L), 1M aq. NaOH (100 mL), 5% aq. NaHCO3 (250 mL), and brine (250 mL)
  5. dry with materialAfter drying over Na2SO4 and filtration
  6. customthe solvent was removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-90e6a9f571f94fa9883cabf30cdd2454
Source dataset
uspto-grants-2012_07
Patent number
US08211935B2

Reaction notes

Loading…