Toluene → Ethyl 5-nitro-1-propyl-1H-indole-2-carboxylate
Reaction equation
C([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=2)[NH:5][C:4]=1[C:15]([OH:17])=[O:16])C.[OH-].[K+].[CH2:20](Br)[CH2:21][CH3:22].[NH4+].[Cl-].[C:26]1(C)C=CC=C[CH:27]=1>CS(C)=O>[CH2:26]([O:17][C:15]([C:4]1[N:5]([CH2:20][CH2:21][CH3:22])[C:6]2[C:11]([CH:3]=1)=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][CH:7]=2)=[O:16])[CH3:27]Participants
7
Procedure
To 3.69 g (15.75 mmol) of commercial ethyl 5-Nitro-2-carboxy-indole dissolved in 35 mL of DMSO was added 2.01 g (31.5 mmol) of KOH. The reaction was stirred vigourously for 30 mins., at which time 2.86 mL (31.5 mmol) of propyl bromide was added. After 4 hours an additional 5 mL DMSO was added and the reaction was reacted overnight. 1 mL 5% aqueous NH4Cl was added and poured into toluene (150 mL) and washed with saturated NaHCO3 (100 mL). The aqueous layer was extracted twice with toluene (75 mL each) and the combined organic layers washed with brine (100 mL), dried over Na2SO4 and concentrated. The product was dissolved in 100 mL dioxane and freeze-dried to give 4.15 g (15.1 mmol, 95%) of 93.
Workup
- customthe reaction was reacted overnight
- washwashed with saturated NaHCO3 (100 mL)
- extractionThe aqueous layer was extracted twice with toluene (75 mL each)
- washthe combined organic layers washed with brine (100 mL)
- dry with materialdried over Na2SO4
- concentrationconcentrated
- dissolutionThe product was dissolved in 100 mL dioxane
- customfreeze-dried
Sources & evidence
- ORD record
- ord-0d5a328b641e4ec78758a9e16fdeac51
- Source dataset
- uspto-grants-2006_06
- Patent number
- US07064218B2
Reaction notes
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