Stannous chloride dihydrate → HCID 59809535, compound

HRID 2114485Notes

Reaction equation

HRID 2114485 reaction equation
[Br:1][C:2]1[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=1[O:4][C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][C:12]=1[N+:13]([O-])=O)[C:8]#[N:9].O.O.[Sn](Cl)Cl>CO>[NH2:13][C:12]1[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[CH:6][C:5]=1[O:4][C:3]1[CH:16]=[CH:17][CH:18]=[CH:19][C:2]=1[Br:1]

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 59809541HCID 59809541, compound

Product 1

HCID 59809535HCID 59809535, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of 3-(2-bromophenoxy)-4-nitrobenzonitrile, 1 (5 g; 15.67 mmol) in methanol (100 mL) was added tin(II) chloride dihydrate (17.68 g; 78.36 mmol). The mixture was stirred at rt overnight, and the solvent was removed via evaporation. Ethyl acetate (100 mL) and 1N NaOH (100 mL) were added, and the solvents were removed via evaporation. Ethyl acetate (200 mL) was added, and white solid formed. The solid was removed via filtration, washed with ethyl acetate, and the combined filtrates were evaporated. The residue was purified via column chromatography (eluent gradient: 10% to 30% ethyl acetate in heptane) to yield 3.0 g (66%) of 4-amino-3-(2-bromophenoxy)-benzonitrile, 2a. MS m/z (MH+) 288.7/289.7.

Workup

  1. customthe solvent was removed via evaporation
  2. additionEthyl acetate (100 mL) and 1N NaOH (100 mL) were added
  3. customthe solvents were removed via evaporation
  4. additionEthyl acetate (200 mL) was added
  5. customwhite solid formed
  6. customThe solid was removed via filtration
  7. washwashed with ethyl acetate
  8. customthe combined filtrates were evaporated
  9. customThe residue was purified via column chromatography (eluent gradient: 10% to 30% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-b369c2d6eaf94c4ca056c94b5b3e0e2c
Source dataset
uspto-grants-2008_10
Patent number
US07432257B2

Reaction notes

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