3-Methyl-2-butanone → 5-Methoxy-2,3,3-trimethyl-3H-indole

HRID 2105099Notes

Reaction equation

HRID 2105099 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10]N)=[CH:6][CH:5]=1.[CH3:12][CH:13]([CH3:17])[C:14](=O)[CH3:15]>C(O)(=O)C>[CH3:2][O:3][C:4]1[CH:9]=[C:8]2[C:7](=[CH:6][CH:5]=1)[N:10]=[C:14]([CH3:15])[C:13]2([CH3:17])[CH3:12]

Participants

4

Reactant 2

HCID 112513-Methyl-2-butanoneHCID 27239044-Methoxyphenylhydrazine hydrochloride

Product 1

HCID 110953925-Methoxy-2,3,3-trimethyl-3H-indole

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

To 4-methoxyphenyl hydrazine hydrochloride (4.84 g) was added 3-methyl-2-butanone (6.4 ml) and acetic acid (45 ml). The mixture was heated to 100° C. for 2.5 hours after which time the solvent was removed by rotary evaporation. Flash column chromatography gave the product (4.66 g).

Workup

  1. customwas removed by rotary evaporation

Sources & evidence

ORD record
ord-7d5dbc9b7ac1493e878d3c6678a37c17
Source dataset
uspto-grants-2009_08
Patent number
US07579140B2

Reaction notes

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