Water → 2,3-dihydro-1H-indol-1-amine

HRID 1894740Notes

Reaction equation

HRID 1894740 reaction equation
[N:1]([N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4]1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[N:3]1([NH2:1])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4]1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 242741-NitrosoindolineHCID 21226445Aluminium lithium hydride

Product 1

HCID 27609322,3-dihydro-1H-indol-1-amineYield 88.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1-nitroso-2,3-dihydro-1H-indole (5.27 g, 35.6 mmol) in tetrahydrofuran (35 ml) was added dropwise to a refluxing slurry of lithium aluminium hydride (2.98 g, 78.5 mmol) in tetrahydrofuran (100 ml). After 1 hour the mixture was cooled in an ice bath and water (3 ml) carefully added. 2M sodium hydroxide (6 ml) followed by water (6 ml) were added and the mixture heated to reflux for 30 minutes. After cooling to room temperature the precipitate formed was filtered off. The filtrate obtained was evaporated to dryness to yield 2,3-dihydro-indol-1-ylamine as a red/brown oil (4.216 g), which was used for the next step without further purification.

Workup

  1. temperatureAfter 1 hour the mixture was cooled in an ice bath
  2. additionwere added
  3. temperaturethe mixture heated
  4. temperatureto reflux for 30 minutes
  5. customformed
  6. filtrationwas filtered off
  7. customThe filtrate obtained
  8. customwas evaporated to dryness

Sources & evidence

ORD record
ord-7d5d622462494fa099fb951280da1e4d
Source dataset
uspto-grants-2013_08
Patent number
US08513292B2

Reaction notes

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