1H-indol-4-ol → Indoline

HRID 1987464Notes

Reaction equation

HRID 1987464 reaction equation
O[C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2.C([BH3-])#N.[Na+]>C(O)(=O)C>[NH:6]1[C:7]2[C:3](=[CH:2][CH:10]=[CH:9][CH:8]=2)[CH2:4][CH2:5]1

Participants

4

Reactant 2

HCID 754211H-indol-4-olHCID 5003444Sodium cyanoborohydride

Product 1

HCID 10328Indoline

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

4-Hydroxyindole was reduced with sodium cyanoborohydride and acetic acid to give 4-hydroxy, dihydroindole. A mixture of ethyl iodide (40 ml), potassium carbonate (1.09 gm, 7.8 mmole) and 4-hydroxy, dihydroindole (1.06 gm, 7.8 mmole) was refluxed for 2 hr. Excess ethyl iodide was evaporated under vacuum, water was added (10 ml) and the product was extracted with dichloromethane. Silica gel chromatography gave N-ethyl-4-hydroxy-dihydroindole (0.30 gm, 23% yield) as a pale yellow solid.

Sources & evidence

ORD record
ord-e54b68ca4d5e4b07baf13261421d15e4
Source dataset
uspto-grants-2009_06
Patent number
US07550570B2

Reaction notes

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