Sodium Chloride → 7-ethyl-2-methyl-1H-indole

HRID 890236Notes

Reaction equation

HRID 890236 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N+:9]([O-])=O)[CH3:2].[C:12]([Mg]Br)([CH3:14])=[CH2:13].[Na+].[Cl-]>C1COCC1>[CH3:14][C:12]1[NH:9][C:4]2[C:5]([CH:13]=1)=[CH:6][CH:7]=[CH:8][C:3]=2[CH2:1][CH3:2]

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 691561-Ethyl-2-nitrobenzeneHCID 178456138HCID 178456138, compound

Product 1

HCID 222505877-ethyl-2-methyl-1H-indole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-20 °C

Procedure

A solution of 36.5 g of 2-ethylnitrobenzene in 250 ml of THF is added dropwise at −20° C. to 1.6 l of 0.5M isopropenylmagnesium bromide in THF. The reaction medium is maintained at −20° C. with stirring for 2 hours and then the medium is poured onto 800 ml of saturated NaCl solution. The mixture is allowed to separate by settling and then extraction is carried out with ether. The ether extract is dried and evaporated and then the residue is chromatographed on silica while eluting with an AcOEt/cyclohexane (1/9, v/v) mixture. 23.75 g of the expected compound are obtained.

Workup

  1. customto separate
  2. extractionextraction
  3. extractionThe ether extract
  4. customis dried
  5. customevaporated
  6. customthe residue is chromatographed on silica
  7. washwhile eluting with an AcOEt/cyclohexane (1/9, v/v) mixture

Sources & evidence

ORD record
ord-bea267bd53d245be8521dee4a2e95693
Source dataset
uspto-grants-2006_02
Patent number
US06995184B2

Reaction notes

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