Hydrochloric Acid → 6-Azaindole

HRID 1490243Notes

Reaction equation

HRID 1490243 reaction equation
C(OC([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[N:14][CH:15]=2)[CH2:10][CH:9]1O)=O)(C)(C)C.Cl.[OH-].[Na+]>O1CCCC1>[NH:8]1[C:16]2=[CH:15][N:14]=[CH:13][CH:12]=[C:11]2[CH:10]=[CH:9]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 10922518HCID 10922518, compound

Product 1

HCID 92196-Azaindole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

The azaindoline (step b, 1.1 g, 5.0 mmol) was dissolved in tetrahydrofuran (20 ml) and treated with 5.5M hydrochloric acid (5 ml). The mixture was heated at 50° C. for 4.5 hours cooled to 0° C. and basified with 5M sodium hydroxide (7.0 ml). The mixture was extracted with ethyl acetate (2×20 ml) and the combined ethyl acetate fractions were washed with saturated brine (20 ml), dried (Na2SO4), filtered and concentrated in vacuo to afford the title compound as a pale yellow crystalline solid; yield: 0.57 g (97%). mp. 132°-134° C.[Lit. mp 131°-132° C.].

Workup

  1. temperaturecooled to 0° C.
  2. extractionThe mixture was extracted with ethyl acetate (2×20 ml)
  3. washthe combined ethyl acetate fractions were washed with saturated brine (20 ml)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0652b9c08d2d4c839124c5d6edbaa19a
Source dataset
uspto-grants-1997_10
Patent number
US05681959

Reaction notes

Loading…