Sulfamic Acid → 9-Phenanthrenecarboxylic acid

HRID 1929542Notes

Reaction equation

HRID 1929542 reaction equation
N[C:2](=[CH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:3]([OH:5])=[O:4].[OH-].[Na+].N([O-])=O.[Na+].F[B-](F)(F)F.[H+].S(=O)(=O)(O)N>O.CC(C)=O.[CH-]1C=CC=C1.[CH-]1C=CC=C1.[Fe+2]>[CH:12]1[C:7]2[CH:6]=[C:2]([C:3]([OH:5])=[O:4])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:8]=2[CH:9]=[CH:10][CH:11]=1

Participants

9

Reactant 5

HCID 5987Sulfamic AcidHCID 14798Sodium HydroxideHCID 28118Tetrafluoroboric acidHCID 193432HCID 193432, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 947659-Phenanthrenecarboxylic acid

Reagents, catalysts & solvents 3

HCID 7611Bis(eta-cyclopentadienyl) ironCatalystHCID 180AcetoneSolventHCID 962WaterSolvent2×

Procedure

A solution composed of the aminocinnamic acid (3 mmol), NaOH (33 mmol) and NaNO2 in water (10 mL) was added dropwise over 30 min with stirring to 48% fluoroboric acid (43 mmol) at 0-5° C. The mixture was stirred for 1 h, after which sulfamic acid was added until the mixture tested negative to starch-iodide paper. The crude solid was collected by filtration, dissolved in anhydrous acetone (10 mL) and then added dropwise with stirring over a 15 min period to ferrocene (0.056 g, 0.3 mmol) in acetone at rt. After an additional 15 min of stirring, the green reaction mixture was added to water (100 mL). A light-yellow precipitate was collected and the trace amount of ferrocene was removed in vacuo to afford the phenanthrene-9-carboxylic acid.

Workup

  1. additionwas added dropwise over 30 min
  2. filtrationThe crude solid was collected by filtration
  3. dissolutiondissolved in anhydrous acetone (10 mL)
  4. additionadded dropwise
  5. stirringAfter an additional 15 min of stirring
  6. customA light-yellow precipitate was collected
  7. customthe trace amount of ferrocene was removed in vacuo

Sources & evidence

ORD record
ord-3493f3174e2848e3ac6298634987eb14
Source dataset
uspto-grants-2012_05
Patent number
US08188089B2

Reaction notes

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