Methanol → 4-{n-[2-Hydroxy-3-(n,n-dimethylamino)propyl]-n-methylamino}nitrobenzene

HRID 1357553Notes

Reaction equation

HRID 1357553 reaction equation
[H-].[Na+].[N+:3]([C:6]1[CH:13]=[CH:12][C:9]([NH:10][CH3:11])=[CH:8][CH:7]=1)([O-:5])=[O:4].[CH2:14]([CH:16]1[O:18][CH2:17]1)Br.CO.[CH3:21][N:22](C=O)[CH3:23]>CNC>[OH:18][CH:16]([CH2:17][N:22]([CH3:23])[CH3:21])[CH2:14][N:10]([C:9]1[CH:12]=[CH:13][C:6]([N+:3]([O-:5])=[O:4])=[CH:7][CH:8]=1)[CH3:11]

Participants

7

Reactant 5

HCID 887MethanolHCID 6228DimethylformamideHCID 7483N-Methyl-4-nitroanilineHCID 18430EpibromohydrinHCID 24758Sodium hydride

Product 1

HCID 181865034-{n-[2-Hydroxy-3-(n,n-dimethylamino)propyl]-n-methylamino}nitrobenzeneYield 86%

Reagents, catalysts & solvents 1

HCID 674DimethylamineSolvent

Procedure

Sodium hydride (60% dispersion in oil; 290 mg, 7.2 mmol) was added portionwise over 30 minutes to a solution of 4-nitro-N-methylaniline (1.0 g, 6.6 mmol) in DMF (30 ml) at 0° C. Epibromohydrin (0.62 ml, 7.2 mmol) was added dropwise to the solution at 0° C. and the mixture was left to stand overnight. Volatile material was removed by evaporation and the residue was dissolved in a solution of dimethylamine in methanol (5.6M, 132 mmol). The solution was left to stand for 12 hours and then concentrated. The residue was dissolved in DCM (200 ml) and the solution was washed with water (3×20 ml) and saturated sodium chloride (20 ml) and dried. Evaporation gave the product as an orange solid (1.44 g, 86%). MS (MH+): 254.

Workup

  1. waitthe mixture was left
  2. customVolatile material was removed by evaporation
  3. waitThe solution was left
  4. waitto stand for 12 hours
  5. concentrationconcentrated
  6. dissolutionThe residue was dissolved in DCM (200 ml)
  7. washthe solution was washed with water (3×20 ml) and saturated sodium chloride (20 ml)
  8. customdried
  9. customEvaporation

Sources & evidence

ORD record
ord-38f0f4c11c50427984c5582a7b4b5413
Source dataset
uspto-grants-2003_07
Patent number
US06593326B1

Reaction notes

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