Ethanol → 1,3-Dioxaindane-4-carboxylic acid

HRID 1419092Notes

Reaction equation

HRID 1419092 reaction equation
[CH2:1]1[O:13][C:12]2[CH:11]=[C:10]3[C:5](C(=O)C(C(=O)C(F)(F)F)SC3)=[CH:4][C:3]=2[O:2]1.C1C(NN)=CC=C(S(N)(=O)=[O:30])C=1.Cl.[CH2:34]([OH:36])C>>[CH2:1]1[O:2][C:3]2[C:12](=[C:11]([CH:10]=[CH:5][CH:4]=2)[C:34]([OH:36])=[O:30])[O:13]1

Participants

4

Reactant 3

HCID 702EthanolHCID 27945674-Hydrazinylbenzenesulfonamide hydrochlorideHCID 67593394HCID 67593394, compound

Product 1

HCID 3048321,3-Dioxaindane-4-carboxylic acid

Procedure

6,7-Methylenedioxy-3-(trifluoroacetyl)isothiochroman-4-one from Step 6 (0.64 g, 2.1 mmol) was dissolved in ethanol (100 mL) and 4-sulfonamidophenylhydrazine hydrochloride (0.56 g, 2.5 mmol) was added. The mixture was heated to reflux for 16 hours, and concentrated. The resultant oily solid was dissolved in ethyl acetate and washed with brine and water, dried over MgSO4 and concentrated. Purification was achieved by flash column chromatography eluting with (1:1) ethyl acetate:hexanes. The appropriate fractions were concentrated and recrystallized from ethyl acetate/hexanes. The product was a light brown solid (0.2 g, 21%): mp 272°14 274° C. 1H NMR (DMSO-d6 300 MHz ) 7.98 (d, J=8.4 Hz, 2H), 7.78 (d, J=8.7 Hz, 2H), 7.44 (bs, 2H), 6.79 (d, J=8.4 Hz, 1H), 6.28 (d, J=8.1 Hz, 1H), 6.14 (s, 2H), 4.09 (s, 2H). Anal.s calc'd for C18H12N3S2O4F3 : C, 47.47; H, 2.66; N, 9.23. Found: C, 47.56; H, 2.73; N, 9.16.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 16 hours
  3. concentrationconcentrated
  4. dissolutionThe resultant oily solid was dissolved in ethyl acetate
  5. washwashed with brine and water
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. customPurification
  9. washeluting with (1:1) ethyl acetate
  10. concentrationThe appropriate fractions were concentrated
  11. customrecrystallized from ethyl acetate/hexanes
  12. custommp 272°14 274° C

Sources & evidence

ORD record
ord-04cfc8adc3cf47f08103a8cf0395b7fb
Source dataset
uspto-grants-1999_03
Patent number
US05886016

Reaction notes

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