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

HRID 2263530Notes

Reaction equation

HRID 2263530 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 has been attained. The mixture is extracted with tert-butyl methyl ether (3×). The combined organic phases are dried with 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. extractionThe mixture is extracted with tert-butyl methyl ether (3×)
  6. dry with materialThe combined organic phases are dried with sodium sulphate
  7. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-f2fd000caa8a44e0aaf3078c14ce78b0
Source dataset
uspto-grants-2010_12
Patent number
US07851634B2

Reaction notes

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