Water → HCID 19086744, compound

HRID 1464566Notes

Reaction equation

HRID 1464566 reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[N:9][NH:10]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[H-].[Na+].Br[CH:16]([CH3:22])[C:17]([O:19][CH2:20][CH3:21])=[O:18].O>CN(C=O)C>[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[N:9][N:10]2[CH:16]([CH3:22])[C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 962WaterHCID 242396-NitroindazoleHCID 24758Sodium hydrideHCID 79040Ethyl 2-bromopropionate

Product 1

HCID 19086744HCID 19086744, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-Nitroindazole (10 g) was dissolved in dry DMF (200cm3) and 50% sodium hydride (2.94 g) added portionwise with stirring. After 20 minutes ethyl 2-bromopropionate (8cm3) was added and the mixture stirred at room temperature for 4 hours, poured into water (1L) and extracted with ethyl acetate four times. The combined organic extracts were washed with water, dried (MgSO4), filtered and the filtrate concentrated under vacuum. The residue was purified by chromatography (SiO2 ; hexane: t-butylmethyl ether, 7:3) to give ethyl 2-(6-nitroindazol-1-yl)propionate (1.3 g) m.p. 99.7°-100.1° C.; M+ =263;

Workup

  1. stirringthe mixture stirred at room temperature for 4 hours
  2. extractionextracted with ethyl acetate four times
  3. washThe combined organic extracts were washed with water
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated under vacuum
  7. customThe residue was purified by chromatography (SiO2 ; hexane: t-butylmethyl ether, 7:3)

Sources & evidence

ORD record
ord-211ec4b5e31041e2b1b138d722db41c6
Source dataset
uspto-grants-1994_04
Patent number
US05306692

Reaction notes

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