1H-Indole, 1-ethyl-2-methyl- → 1-Ethyl-2-methyl-3-(4-methyl-1-napthoyl)indole

HRID 574599Notes

Reaction equation

HRID 574599 reaction equation
[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]1[CH3:12])[CH3:2].[Cl-].C[Al+]C.[CH3:17][C:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:21]([C:28](Cl)=[O:29])=[CH:20][CH:19]=1>ClCCl>[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:28]([C:21]2[C:22]3[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:18]([CH3:17])=[CH:19][CH:20]=2)=[O:29])=[C:4]1[CH3:12])[CH3:2]

Participants

5

Reactant 3

HCID 1704321H-Indole, 1-ethyl-2-methyl-HCID 16686359Dimethylalumanylium chlorideHCID 248874124-Methylnaphthalene-1-carbonyl chloride

Product 1

HCID 566496961-Ethyl-2-methyl-3-(4-methyl-1-napthoyl)indole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 0.20 g (1.26 mmol) of 1-ethyl-2-methylindole in 4 mL of dry dichloromethane at 0° C. under argon, was added dropwise 0.17 g (1.89 mmol) of dimethylaluminum chloride. The solution was stirred at this temperature for 45 min and then 0.39 g (1.88 mmol) of 4-methyl-1-napthoyl chloride in 6 mL of dry dichloromethane was added, and the solution stirred at 0° C. for 4 hrs. The solution was carefully quenched by the addition of 1M HCl and extracted with dichloromethane (2×20 mL). The combined organic extract were washed with a saturated solution of NaHCO3, H2O, brine, dried (MgSO4), filtered and concentrated in vacuo. The oil was purified by chromatography (ethyl acetate/petroleum ether 1:9) to afford the desired compound as an orange solid 0.16 g (40%), recrystallization from petroleum ether/ether provided white crystals, mp 136-137° C.: 1H NMR (300 MHz, CDCl3) δ 1.42 (t, J=7.3 Hz, 3H), 2.51 (s, 3H), 2.80 (s, 3H), 4.25 (q, J=7.3 Hz, 2H), 6.92-7.05 (m, 1H), 7.17-7.29 (m, 2H), 7.32-7.39 (m, 2H), 7.46-7.53 (m, 2H), 7.54-7.61 (m, 1H), 8.11 (d, J=8.3 Hz, 1H), 8.21 (d, J=8.3 Hz, 1H); 13C NMR (300 MHz, CDCl3) δ 12.3, 14.75, 19.9, 38.0, 109.2, 115.1, 121.4, 121.9, 122.2, 124.3, 125.8, 126.1, 126.3, 126.5, 127.3, 130.5, 132.9, 135.6, 136.7, 138.9, 145.1, 193.6; GC/MS (EI) m/z (rel intensity) 327 (100), 312 (80), 186 (60), 115 (20). Anal. Calcd for C23H21NO: C, 84.37; H, 6.46; N, 4.28. Found C23H21NO: C, 84.23; H, 6.48; N, 4.29.

Workup

  1. stirringthe solution stirred at 0° C. for 4 hrs
  2. customThe solution was carefully quenched by the addition of 1M HCl
  3. extractionextracted with dichloromethane (2×20 mL)
  4. extractionThe combined organic extract
  5. washwere washed with a saturated solution of NaHCO3, H2O, brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe oil was purified by chromatography (ethyl acetate/petroleum ether 1:9)
  10. customto afford
  11. customthe desired compound as an orange solid 0.16 g (40%), recrystallization from petroleum ether/ether provided white crystals, mp 136-137° C.

Sources & evidence

ORD record
ord-98666d2672744982ba08661ae8e1ad6d
Source dataset
uspto-grants-2015_05
Patent number
US09034895B2

Reaction notes

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