Sodium Dithionite → HCID 178422420, compound

HRID 1781237Notes

Reaction equation

HRID 1781237 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH3:14])[CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([OH:12])[CH:8]=[N+:7]2[O-].S(S([O-])=O)([O-])=O.[Na+].[Na+]>C(O)C.O>[Br:1][C:2]1[CH:3]=[C:4]([CH3:14])[CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([OH:12])[CH:8]=[N:7]2

Participants

5

Reactant 2

HCID 24489Sodium DithioniteHCID 178422421HCID 178422421, compound

Product 1

HCID 178422420HCID 178422420, compoundYield 65.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

The title compound of Step C (25 g, 98 mmol) and sodium dithionite (38 g, 220 mmol) were suspended in a mixture of ethanol (1000 mL) and water (200 mL) at room temperature. After 1 h, most of the solvent was removed under reduced pressure. The residue was diluted with water and acidified with hydrochloric acid. Insolubles were removed by filtration. The filtrate was extracted twice with methylene chloride. The combined organic extracts were dried (MgSO4), filtered, and concentrated under reduced pressure to afford the title compound of Step D as a tan/yellow solid (15.29 g, 65%). 1H NMR (CDCl3): δ2.37 (s,3H), 7.5 (d,2H), 8.15 (s, 1H), 9.8 (br s, 1H).

Workup

  1. custommost of the solvent was removed under reduced pressure
  2. additionThe residue was diluted with water
  3. customInsolubles were removed by filtration
  4. extractionThe filtrate was extracted twice with methylene chloride
  5. dry with materialThe combined organic extracts were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ac830d54b7724a8b93da7678034827fa
Source dataset
uspto-grants-1997_05
Patent number
US05633218

Reaction notes

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