Theophylline → HCID 69028523, compound

HRID 2104301Notes

Reaction equation

HRID 2104301 reaction equation
[N:1]1([C:12](=[O:13])[C:11]2[NH:10][CH:9]=[N:8][C:7]=2[N:5]([CH3:6])[C:3]1=[O:4])[CH3:2].[N+:14]([C:17]1[CH:22]=[CH:21][C:20](CCBr)=[CH:19][CH:18]=1)([O-:16])=[O:15].[OH-].[Na+].[CH:28]([OH:31])(C)[CH3:29]>O>[CH3:2][N:1]1[C:12](=[O:13])[C:11]2[N:10]([C:20]3[CH:19]=[CH:18][C:17]([N+:14]([O-:16])=[O:15])([O:31][CH2:28][CH3:29])[CH2:22][CH:21]=3)[CH:9]=[N:8][C:7]=2[N:5]([CH3:6])[C:3]1=[O:4]

Participants

6

Reactant 4

HCID 2153TheophyllineHCID 3776IsopropanolHCID 14798Sodium HydroxideHCID 792664-Nitrophenethyl bromide

Product 1

HCID 69028523HCID 69028523, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 0.59 g (3.26 mmol) of theophylline, 1.5 g (6.52 mmol) of 2-(4-nitrophenyl)ethyl bromide, 0.13 g (3.26 mmol) of NaOH pellets in 4 ml of water and 8 ml of isopropanol is heated to reflux for 24 hours. After returning to 23° C., the insoluble portion is filtered and the filtrate is extracted with 25 ml of CH2Cl2. The organic phase is washed with 10 ml of water followed by 10 ml of brine. After drying over sodium sulphate, filtration and concentration to dryness, the residue is purified on a silica column (eluent: CH2Cl2/MeOH: 95/5). A white solid is obtained with a yield of 50%.

Workup

  1. temperatureto reflux for 24 hours
  2. customAfter returning to 23° C.
  3. filtrationthe insoluble portion is filtered
  4. extractionthe filtrate is extracted with 25 ml of CH2Cl2
  5. washThe organic phase is washed with 10 ml of water
  6. dry with materialAfter drying over sodium sulphate, filtration and concentration to dryness
  7. customthe residue is purified on a silica column (eluent: CH2Cl2/MeOH: 95/5)
  8. customA white solid is obtained with a yield of 50%

Sources & evidence

ORD record
ord-8d7031d727f140fcb0c699c1bf812a6a
Source dataset
uspto-grants-2009_08
Patent number
US07576241B2

Reaction notes

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