Allyl bromide → HCID 19702703, compound

HRID 1451681Notes

Reaction equation

HRID 1451681 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 1 M 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-42046b1e57254ce69eb392c1a0746e42
Source dataset
uspto-grants-1997_02
Patent number
US05605726

Reaction notes

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