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

HRID 890234Notes

Reaction equation

HRID 890234 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

42.1 g of 2-chloronitrobenzene are placed in 850 ml of THF under a nitrogen atmosphere. The mixture is cooled to −40° C. and then 1.61 of 0.5M isopropenylmagnesium bromide in THF are added dropwise. After stirring at −40° C. for 1 hour, the mixture is hydrolysed with 400 ml of a 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 while eluting with toluene. 20.3 g of the expected compound are obtained.

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. washwhile eluting with toluene

Sources & evidence

ORD record
ord-e351a1fcc9084239a1e475239f2a9247
Source dataset
uspto-grants-2006_02
Patent number
US06995184B2

Reaction notes

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