hydroxylamine-O-sulfonic acid → HCID 14372125, compound

HRID 1382987Notes

Reaction equation

HRID 1382987 reaction equation
[Cl:1][C:2]1[C:7]2[CH:8]=[CH:9][O:10][C:6]=2[CH:5]=[CH:4][N:3]=1.C([N-:14]C(C)C)(C)C.[Li+].O.O.O.C([O-])(=O)C.[Na+].N[O:28][S:29]([OH:32])(=O)=O>O1CCCC1>[S:29]([C:9]1[O:10][C:6]2[CH:5]=[CH:4][N:3]=[C:2]([Cl:1])[C:7]=2[CH:8]=1)(=[O:32])(=[O:28])[NH2:14]

Participants

6

Reactant 4

HCID 76284hydroxylamine-O-sulfonic acidHCID 2724682Lithium diisopropylamideHCID 27797464-Chlorofuro[3,2-c]pyridineHCID 23665404Sodium Acetate Trihydrate

Product 1

HCID 14372125HCID 14372125, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 4-chloro-furo[3,2-c]pyridine (6.17 g, 40.2 mmol) in tetrahydrofuran (80 ml), under a nitrogen atmosphere at -70° C., was added dropwise a solution of 0.7M lithium diisopropylamide in THF (64 ml, 44.8 mmol). After stirring for 1/2 hour, sulfur dioxide gas was bubbled over the surface of the reaction and the temperature was allowed to gradually rise to room temperature. Dilution with diethyl ether (150 ml) caused the lithium sulfinate intermediate to precipitate. This precipitate (15 g) was collected by filtration and dissolved in water (80 ml). After addition of sodium acetate trihydrate (21.6 g, 0.26 mol) and hydroxylamine-O-sulfonic acid (10.4 g, 0.088 mol), mixture was stirred for 18 hours as the product slowly precipitated. The precipitated crude product was collected by filtration, dissolved in ethyl acetate/methanol. This solution was dried over anhydrous sodium sulfate, filtered through a pad of charcoal and evaporated to give pure crystalline product (5.25 g, 56% yield). Recrystallization of this material from ethyl acetate gave product with m.p. 192°-194° C.

Workup

  1. customsulfur dioxide gas was bubbled over the surface of the reaction
  2. customto gradually rise to room temperature
  3. customto precipitate
  4. filtrationThis precipitate (15 g) was collected by filtration
  5. dissolutiondissolved in water (80 ml)
  6. stirringwas stirred for 18 hours as the product
  7. customslowly precipitated
  8. customThe precipitated crude product
  9. filtrationwas collected by filtration
  10. dissolutiondissolved in ethyl acetate/methanol
  11. dry with materialThis solution was dried over anhydrous sodium sulfate
  12. filtrationfiltered through a pad of charcoal
  13. customevaporated

Sources & evidence

ORD record
ord-cd5487cb2cc345bf90cf5d7680b9bc42
Source dataset
uspto-grants-1989_02
Patent number
US04808595

Reaction notes

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