Stannous Chloride → 5-bromo-N1-(3-methoxypropyl)benzene-1,2-diamine

HRID 252344Notes

Reaction equation

HRID 252344 reaction equation
[Sn](Cl)Cl.[Br:4][C:5]1[CH:6]=[CH:7][C:8]([N+:17]([O-])=O)=[C:9]([NH:11][CH2:12][CH2:13][CH2:14][O:15][CH3:16])[CH:10]=1>C(O)C>[Br:4][C:5]1[CH:10]=[C:9]([NH:11][CH2:12][CH2:13][CH2:14][O:15][CH3:16])[C:8]([NH2:17])=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 24479Stannous ChlorideHCID 65341496(5-Bromo-2-nitrophenyl)(3-methoxypropyl)amine

Product 1

HCID 653434125-bromo-N1-(3-methoxypropyl)benzene-1,2-diamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

78.57 g of tin(II) chloride are added to a solution of 21.01 g of (5-bromo-2-nitrophenyl)-(3-methoxypropyl)amine in 950 ml of ethanol. The reaction mixture is heated to reflux for 12 hours. The mixture is cooled to room temperature and concentrated by evaporation. The residue is treated with 2M NaOH until a pH of 11 is obtained. The mixture is extracted with tert-butyl methyl ether (3×). The combined organic phases are dried over sodium sulphate and concentrated by evaporation. The title compound is obtained as an orange oil from the residue. Rf=0.31 (1:1 EtOAc-heptane). Rt=3.06 (gradient I).

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux for 12 hours
  3. concentrationconcentrated by evaporation
  4. additionThe residue is treated with 2M NaOH until a pH of 11
  5. customis obtained
  6. extractionThe mixture is extracted with tert-butyl methyl ether (3×)
  7. dry with materialThe combined organic phases are dried over sodium sulphate
  8. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-97d0f0415c8b4bd88ea658bf23a148de
Source dataset
uspto-grants-2011_01
Patent number
US07868036B2

Reaction notes

Loading…