Stannous chloride dihydrate → HCID 22669713, compound

HRID 1007476Notes

Reaction equation

HRID 1007476 reaction equation
[Cl:1][C:2]1[CH:20]=[C:19]([N+:21]([O-])=O)[CH:18]=[C:17]([Cl:24])[C:3]=1[O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][CH:9]=[C:8]2[CH:14]([CH3:16])[CH3:15].O.O.[Sn](Cl)Cl>CN1C(=O)CCC1>[Cl:24][C:17]1[CH:18]=[C:19]([CH:20]=[C:2]([Cl:1])[C:3]=1[O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][CH:9]=[C:8]2[CH:14]([CH3:15])[CH3:16])[NH2:21]

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 22669500HCID 22669500, compound

Product 1

HCID 22669713HCID 22669713, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

500 mg of 5-(2,6-dichloro-4-nitrophenoxy)-3-isopropyl-1H-indole (Example I) are stirred with 6.18 g of tin(II) chloride dihydrate in 5 ml of NMP for 17 hours at 50° C. The solvent is removed in vacuo and the residue is taken up in ethyl acetate. The mixture is washed with saturated ammonium chloride solution and saturated sodium chloride solution, the organic phase is dried and the solvent is removed in vacuo. The product is precipitated with diethyl ether. By chromatographic purification (cyclohexane/ethyl acetate) of the solid, 174 mg of 3,5-dichloro-4-[(3-isopropyl-1H-indol-5-yl)oxy]aniline are obtained.

Workup

  1. customThe solvent is removed in vacuo
  2. washThe mixture is washed with saturated ammonium chloride solution and saturated sodium chloride solution
  3. customthe organic phase is dried
  4. customthe solvent is removed in vacuo
  5. customThe product is precipitated with diethyl ether
  6. customBy chromatographic purification (cyclohexane/ethyl acetate) of the solid, 174 mg of 3,5-dichloro-4-[(3-isopropyl-1H-indol-5-yl)oxy]aniline
  7. customare obtained

Sources & evidence

ORD record
ord-6bfb74269d134d828ee709efcfee3145
Source dataset
uspto-grants-2004_09
Patent number
US06794406B2

Reaction notes

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