Water → HCID 67285626, compound

HRID 1947425Notes

Reaction equation

HRID 1947425 reaction equation
[C:1]1([C:7]2[NH:8][C:9]3[C:14]([CH:15]=2)=[CH:13][C:12]([N+:16]([O-:18])=[O:17])=[CH:11][CH:10]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:26][CH2:27][CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30].O>CC#N>[N+:16]([C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:26][CH2:27][CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])[C:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)=[CH:15]2)([O-:18])=[O:17]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 76300Ethyl 4-bromobutyrateHCID 2803095-Nitro-2-phenyl-1H-indole

Product 1

HCID 67285626HCID 67285626, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 2-phenyl-5-nitroindole (prepared as described in J. Org. Chem. (1966), 31(1), 65-9) (1.5 g; 6.3 mmol) in CH3CN (50 ml) was added K2CO3(1.7 g; 12.6 mmol). To the mixture thus obtained was then added dropwise ethyl 4-bromobutanoate (3.3 g; 16 mmol) and the resulting mixture was heated to 120° C. under stirring for 18 hours. After cooling, the mixture was poured into water (500 ml) and the crude product was filtered, dried under vacuum to give ethyl 4-(5-nitro-2-phenyl-1H-indol-1-yl)butanoate which was used in the following reaction without any further purification.

Workup

  1. customTo the mixture thus obtained
  2. temperatureAfter cooling
  3. filtrationthe crude product was filtered
  4. customdried under vacuum

Sources & evidence

ORD record
ord-c135769ca83f41e48415971ebd3ba03f
Source dataset
uspto-grants-2013_03
Patent number
US08399477B2

Reaction notes

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