3-methylsulfanyl-1H-indole → Indole

HRID 1730295Notes

Reaction equation

HRID 1730295 reaction equation
CS[C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5][CH:4]=1>[Ni]>[NH:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH:3]=[CH:4]1

Participants

3

Reactant 1

HCID 108882523-methylsulfanyl-1H-indole

Product 1

HCID 798Indole

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

Conversion of the dimethyl acetal from part A to 3-methylthioindole was accomplished by stirring 0.50 g (2.20 mmol) of the dimethylacetal dissolved in 25 ml of ethyl ether for 2 hr. with 10 ml of 0.5 N aqueous hydrogen chloride. The ethereal layer was separated, treated with a saturated sodium bicarbonate solution, dried, filtered and evaporated to yield 0.35 g (2.14 mmol, 97%) of the oily 3-methylthioindole. This 3-methylthioindole was treated with Raney nickel as described to form indole, identified by comparison with an authentic sample.

Sources & evidence

ORD record
ord-7b04caff6cf642d49e43299fa1004515
Source dataset
uspto-grants-1976_11
Patent number
US03992392

Reaction notes

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