Sodium Hydroxide → 7-Fluoro-2,3-dihydro-1H-indole

HRID 2353458

Reaction equation

HRID 2353458 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][CH:8]=[CH:7]2.C([BH3-])#N.[Na+].[OH-].[Na+]>C(O)(=O)C>[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][CH2:8][CH2:7]2

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 27745047-Fluoro-1H-indoleHCID 5003444Sodium cyanoborohydride

Product 1

HCID 167682617-Fluoro-2,3-dihydro-1H-indoleYield 54.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

7-fluoroindole (2.0 g, 14.8 mmol) was dissolved in acetic acid (6 mL) and sodium cyanoborohydride (1.87 g, 29.6 mmol) was added in 5 portions. The mixture was stirred for 1 hour then poured into 150 mL of 2N NaOH. The mixture was extracted with methylene chloride. The organics were combined, washed with brine, dried over anhydrous magnesium sulfate, and concentrated to give 7-fluoroindoline (1.1 g).

Workup

  1. extractionThe mixture was extracted with methylene chloride
  2. washwashed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-74bf08cac423424aa246f19a619d4605
Source dataset
uspto-grants-2010_07
Patent number
US07750038B2

Linked notes

Loading…