Allyl bromide → HCID 19702703, compound

HRID 1656582Notes

Reaction equation

HRID 1656582 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=1[CH2:12][CH2:13][OH:14].[CH2:15](Br)[CH:16]=[CH2:17]>CN1C(=O)CCC1.C(=O)([O-])[O-].[Na+].[Na+]>[CH2:15]([N:2]([CH3:1])[C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=1[CH2:12][CH2:13][OH:14])[CH:16]=[CH2:17]

Participants

5

Reactant 2

HCID 7841Allyl bromideHCID 19702706HCID 19702706, compound

Product 1

HCID 19702703HCID 19702703, compound

Reagents, catalysts & solvents 2

HCID 10340Sodium CarbonateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a solution of N-methyl-2-(2-hydroxyethyl)-4-nitrobenzenamine (4.90 g, 0.025 mol) in NMP (15 ml) is added allyl bromide (4.55 g, 0.037 mol) at room temperature. The mixture is heated to 85°-90° C. for 6 hours and cooled to room temperature. The mixture is diluted with 1M sodium carbonate solution (250 ml) and extracted with ether twice (250 and 150 ml portions). The extracts are washed with water twice, dried over potassium carbonate and concentrated to a solid. The solid is purified by chromatography on silica gel with hexane-tetrahydrofuran solvent to give N-allyl-N-methyl-2-(2-hydroxyethyl)-4-nitrobenzenamine.

Workup

  1. temperatureThe mixture is heated to 85°-90° C. for 6 hours
  2. extractionextracted with ether twice (250 and 150 ml portions)
  3. washThe extracts are washed with water twice
  4. dry with materialdried over potassium carbonate
  5. concentrationconcentrated to a solid
  6. customThe solid is purified by chromatography on silica gel with hexane-tetrahydrofuran solvent

Sources & evidence

ORD record
ord-7e4f9346cc1142c4b50a58f144beae86
Source dataset
uspto-grants-1993_10
Patent number
US05254655

Reaction notes

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