Stannous chloride dihydrate → Cni H1894

HRID 2303589Notes

Reaction equation

HRID 2303589 reaction equation
O.O.[Sn](Cl)Cl.[C:6]([C:9]1[CH:10]=[C:11]([N+:18]([O-])=O)[CH:12]=[C:13]([C:15](=[O:17])[CH3:16])[CH:14]=1)(=[O:8])[CH3:7]>Cl>[C:6]([C:9]1[CH:10]=[C:11]([CH:12]=[C:13]([C:15](=[O:17])[CH3:16])[CH:14]=1)[NH2:18])(=[O:8])[CH3:7]

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 184616391,1'-(5-Nitro-1,3-phenylene)di(ethan-1-one)

Product 1

HCID 463010Cni H1894Yield 46.7%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To a stirred solution of tin (II) chloride dihydrate (32.87 grams) in concentrated hydrochloric acid (93 mL) at 50° C. was added 3,5-diacetylnitrobenzene (7.54 grams). The heat was removed immediately and an exotherm occurred. The mixture was stirred for 5 minutes, cooled with an ice bath, and neutralized with saturated potassium carbonate solution. The aqueous phase was extracted with several portions of ethyl acetate, dried over anhydrous sodium sulfate and concentrated in vacuo to afford 3.01 grams of the title compound. 1H NMR δ 7.77 (s, 1), 7.48 (s, 2), 5.16 (br s, 2), 2.55 (s, 6).

Workup

  1. customThe heat was removed immediately
  2. temperaturecooled with an ice bath
  3. extractionThe aqueous phase was extracted with several portions of ethyl acetate
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-99a276237fbf4a8ba6f6391b313b89e7
Source dataset
uspto-grants-2002_08
Patent number
US06433009B1

Reaction notes

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