5-Methylindole → 5-Methylindoline

HRID 645326

Reaction equation

HRID 645326 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.COC1C=C2C(=CC=1)NCC2.C([BH3-])#N.[Na+]>C(O)(=O)C>[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH2:6][CH2:5]2

Participants

5

Reactant 3

HCID 119785-Methylindole2×HCID 5003444Sodium cyanoborohydrideHCID 107019745-methoxy-2,3-dihydro-1H-indole

Product 1

HCID 140236795-MethylindolineYield 99%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

5-Methylindoline was prepared from 5-methylindole using the procedure described for the preparation of 5-methoxyindoline. 5-Methylindole (11 g, 0.0835 mol) in glacial acetic acid (150 mL) in a 1 L 3-necked flask was reduced at 10-15° C. with sodium cyanoborohydride (15.8 g, 0.251 mol). Extraction with ethyl acetate provided 5-methylindoline (11 g, 0.0832 mol, 99% yield) as a thick oil which was used without further purification. The structure was corroborated by NMR spectroscopy.

Workup

  1. extractionExtraction with ethyl acetate

Sources & evidence

ORD record
ord-d01d4c3cbc214279923b9c09f839446b
Source dataset
uspto-grants-2010_04
Patent number
US07704667B2

Linked notes

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