HCID 57698807, compound → HCID 67166341, compound

HRID 552377Notes

Reaction equation

HRID 552377 reaction equation
[CH2:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]([N+:14]([O-])=O)[C:5]=1[C:6]([O:8][CH3:9])=[O:7])[CH:2]=[CH2:3]>C(O)(=O)C.C(O)C.C(OCC)(=O)C.[Fe]>[CH2:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]([NH2:14])[C:5]=1[C:6]([O:8][CH3:9])=[O:7])[CH:2]=[CH2:3]

Participants

6

Reactant 1

HCID 57698807HCID 57698807, compound

Product 1

HCID 67166341HCID 67166341, compound

Reagents, catalysts & solvents 4

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred suspension of Step 1 intermediate (4.2 g, 19.98 mmol) in a mixture of 50% aqueous acetic acid (100 ml) and ethanol (100 ml) was added iron powder (5.3 g, 99.9 g atom) and the mixture was refluxed for 3 h. The mixture was cooled to room temperature and filtered through a celite bed. The filtrate was concentrated and the residue obtained was diluted with ethyl acetate and washed with water (2×50 ml) and dried over anhydrous sodium sulfate. The solvent was evaporated to give 3.2 g of the product as a brown oil; 1H NMR (δ ppm, CDCl3, 300 MHz): 7.15-7.07 (m, 1H); 6.62-6.55 (m, 2H); 5.99-5.82 (m, 1H); 5.05-4.95 (m, 2H); 3.86 (s, 3H); 3.53 (d, J=6.0, 2H).

Workup

  1. temperaturethe mixture was refluxed for 3 h
  2. filtrationfiltered through a celite bed
  3. concentrationThe filtrate was concentrated
  4. customthe residue obtained
  5. washwashed with water (2×50 ml)
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was evaporated

Sources & evidence

ORD record
ord-bd5b187a8b694de4972d74254a8c8132
Source dataset
uspto-grants-2011_05
Patent number
US07951814B2

Reaction notes

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