Stannous Chloride → HCID 67337824, compound

HRID 1260387Notes

Reaction equation

HRID 1260387 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:22])/[CH:10]=[CH:11]/[C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[C:14]([OH:21])[CH:13]=2)[CH:5]=[CH:6][CH:7]=1.Cl[Sn]Cl>CCO>[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:22])/[CH:10]=[CH:11]/[C:12]2[CH:17]=[CH:16][C:15]([NH2:18])=[C:14]([OH:21])[CH:13]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 24479Stannous ChlorideHCID 67338426HCID 67338426, compound

Product 1

HCID 67337824HCID 67337824, compoundYield 61.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(E)-N-(3-Chloro-phenyl)-3-(3-hydroxy-4-nitro-phenyl)-acrylamide (159 mg, 0.5 mmol) was suspended in EtOH (10 ml); SnCl2 (562 g, 2.5 mmol) was added and the mixture refluxed for 1.5 hrs. After cooling to RT, the solvent was evaporated. The residue was worked up with 5% sodium bicarbonate and 10% sodium potassium tartrate solutions, extracted with AcOEt, which was separated, dried and evaporated. The residue was triturated with a 1:1 diethyl ether-petroleum ether mixture, giving 89 mg of (E)-N-(3-chloro-phenyl)-3-(4-amino-3-hydroxy-phenyl)-acrylamide as a yellow solid.

Workup

  1. temperaturethe mixture refluxed for 1.5 hrs
  2. customthe solvent was evaporated
  3. extractionextracted with AcOEt, which
  4. customwas separated
  5. customdried
  6. customevaporated
  7. customThe residue was triturated with a 1:1 diethyl ether-petroleum ether mixture

Sources & evidence

ORD record
ord-919d485f69324ec7bb4629e52f5bd7d7
Source dataset
uspto-grants-2013_06
Patent number
US08470831B2

Reaction notes

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