Hydrochloric Acid → HCID 67081826, compound

HRID 549446Notes

Reaction equation

HRID 549446 reaction equation
[CH3:1][C:2]1([CH3:14])[C:10](=[O:11])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:12]#[N:13])[CH:8]=2)[CH2:3]1.[BH4-].[Na+].Cl>C(O)C>[OH:11][CH:10]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:12]#[N:13])[CH:8]=2)[CH2:3][C:2]1([CH3:14])[CH3:1]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 10910237HCID 10910237, compound2×

Product 1

HCID 67081826HCID 67081826, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of Step A. 2,2-dimethyl-3-oxo-2,3-dihydro-1H-indene-5-carbonitrile (17.8 g, 0.096 mol) in ethanol at 0° C. was added NaBH4 (7.27 g, 0.192 mol) as a solid and the resulting mixture was warmed to rt gradually and stirred for ˜16 h. After cooling to 0° C., aq HCl (1N, 300 mL) was added slowly with vigorously stirring. After additional stirring at 0° C. for 30 min and rt for 2 h, the reaction mixture was concentrated to remove ethanol, then extracted with EtOAc (400 mL). The aqueous portion was further extracted with EtOAc (100 mL×3). The combined organic extracts were washed with water (80 mL×2), sat. aq. NaHCO3 (80 mL), brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure to give the title compound as a colorless oil. HPLC Ret. time: 2.62 min. LCMS MH+ (m/z) 188.33. 1H NMR: (DMSO-d6, 400 MHz): δ 7.65 (s, 1H), 7.62 (d, 1H), 7.38 (d, 1H), 5.49 (d, 1H), 4.59 (d, 1H), 2.70 (m, 2H), 1.13 (s, 3H), 0.83 (s, 3H).

Workup

  1. temperatureAfter cooling to 0° C.
  2. stirringwith vigorously stirring
  3. stirringAfter additional stirring at 0° C. for 30 min and rt for 2 h
  4. concentrationthe reaction mixture was concentrated
  5. customto remove ethanol
  6. extractionextracted with EtOAc (400 mL)
  7. extractionThe aqueous portion was further extracted with EtOAc (100 mL×3)
  8. washThe combined organic extracts were washed with water (80 mL×2), sat. aq. NaHCO3 (80 mL), brine
  9. dry with materialdried over magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2d92da78ac49466997eaffe9017b25ea
Source dataset
uspto-grants-2011_05
Patent number
US07943658B2

Reaction notes

Loading…