Tetrahydrofuran → HCID 59737575, compound

HRID 1907711Notes

Reaction equation

HRID 1907711 reaction equation
[CH3:1][O:2][C:3]1[CH:25]=[CH:24][C:6]([C:7]([NH:9][C:10]2[CH:15]=[C:14]([C:16]3[NH:17][CH:18]=[CH:19][CH:20]=3)[CH:13]=[CH:12][C:11]=2[N+:21]([O-])=O)=[O:8])=[CH:5][CH:4]=1.C1COCC1.O.O.[Sn](Cl)Cl.C([O-])(=O)C.[NH4+]>CCOC(C)=O.O.CO>[NH2:21][C:11]1[CH:12]=[CH:13][C:14]([C:16]2[NH:17][CH:18]=[CH:19][CH:20]=2)=[CH:15][C:10]=1[NH:9][C:7](=[O:8])[C:6]1[CH:24]=[CH:25][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1

Participants

8

Reactant 4

HCID 8028TetrahydrofuranHCID 61436Stannous chloride dihydrateHCID 517165Ammonium AcetateHCID 59737421HCID 59737421, compound

Product 1

HCID 59737575HCID 59737575, compoundYield 12%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
55 °C

Procedure

A solution of nitro compound 146 (0.1326 g, 0.39 mmol) in a 8.5:5:1 mixture of THF:MeOH:H2O (14.5 mL) was treated with tin(II) chloride dihydrate (0.602 g, 2.67 mmol) and ammonium acetate (0.818 g, 10.6 mmol) then heated to 55° C. for 60 min. The reaction mixture was cooled to room temperature, diluted with AcOEt, washed with 5% KHSO4, saturated NaHCO3, brine, dried over MgSO4, filtered and concentrated. The title compound 147 was obtained after purification by chromatotron (14.7 mg, 12% yield, eluent: 50% AcOEt in hexane).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. washwashed with 5% KHSO4, saturated NaHCO3, brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c3c29afc35524a8a9f76288dc4050684
Source dataset
uspto-grants-2013_12
Patent number
US08598168B2

Reaction notes

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