Sodium Bicarbonate → HCID 57438335, compound

HRID 1818559Notes

Reaction equation

HRID 1818559 reaction equation
C([SiH2][O:6][C:7](C)(C)[C:8]1[CH:23]=[CH:22][C:11]([C:12]([C:14]2[CH:15]=[N:16][CH:17]=[C:18]([CH:21]=2)[C:19]#[N:20])=[O:13])=[CH:10][CH:9]=1)(C)(C)C.C(=O)(O)[O-].[Na+]>Cl.O1CCCC1>[OH:6][CH2:7][C:8]1[CH:9]=[CH:10][C:11]([C:12]([C:14]2[CH:15]=[N:16][CH:17]=[C:18]([CH:21]=2)[C:19]#[N:20])=[O:13])=[CH:22][CH:23]=1

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 137329420HCID 137329420, compound

Product 1

HCID 57438335HCID 57438335, compoundYield 94.1%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

Dissolve 5-[4-(tert-butyl-dimethyl-silanyloxymethyl)-benzoyl]-nicotinonitrile (510 mg, 1.45 mmol) in 10% aqueous hydrochloric acid (10 mL) and tetrahydrofuran (50 mL) and stir. After 1 hour, add saturated aqueous sodium bicarbonate (50 mL) and extract with ethyl acetate. Combine the organic layers, dry with sodium sulfate, filter and concentrate under reduced pressure to yield the title product as a white solid (325 mg, 94%): 1H NMR (DMSO-d6) δ 4.64 (d, 2H), 5.44 (t, 1H), 7.53 (d, 2H), 7.80 (d, 2H), 8.59 (t, 1H), 9.09 (d, 1H), 9.27 (d, 1H).

Workup

  1. extractionextract with ethyl acetate
  2. dry with materialdry with sodium sulfate
  3. filtrationfilter
  4. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-3f80bdc35b834b21b311459236da6edd
Source dataset
uspto-grants-2009_10
Patent number
US07598423B2

Reaction notes

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