1-Chloro-2-nitrobenzene → 7-chloro-2-methyl-1H-indole

HRID 722398Notes

Reaction equation

HRID 722398 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-])=O.[C:11]([Mg]Br)([CH3:13])=[CH2:12].[NH4+].[Cl-]>C1COCC1>[CH3:13][C:11]1[NH:8][C:3]2[C:4]([CH:12]=1)=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1]

Participants

5

Reactant 3

HCID 69451-Chloro-2-nitrobenzeneHCID 25517Ammonium ChlorideHCID 178456138HCID 178456138, compound

Product 1

HCID 118160627-chloro-2-methyl-1H-indole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-40 °C

Procedure

Under a nitrogen atmosphere 42.1 g of 2-chloronitrobenzene are placed in 850 ml of THF. The mixture is cooled to −40° C. and then 1.6 1 of isopropenylmagnesium bromide at 0.5 M in THF are added dropwise. After 1 hour at −40° C. with stirring the mixture is hydrolyzed with 400 ml of saturated NH4Cl solution. The aqueous phase is extracted twice with ether. The organic phase is dried and then evaporated and the residue is chromatographed on silica, eluting with toluene. This gives 20.3 g of the expected compound.

Workup

  1. extractionThe aqueous phase is extracted twice with ether
  2. customThe organic phase is dried
  3. customevaporated
  4. customthe residue is chromatographed on silica
  5. washeluting with toluene

Sources & evidence

ORD record
ord-a7ff061a5a104dbba7c8ac314afe138e
Source dataset
uspto-grants-2006_11
Patent number
US07138424B2

Reaction notes

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