Sodium Bicarbonate → HCID 57438335, compound

HRID 1161060Notes

Reaction equation

HRID 1161060 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 organic layers, dry over sodium sulfate, filter and concentrate under reduced pressure to yield the title compound 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 materialCombine organic layers, dry over sodium sulfate
  3. filtrationfilter
  4. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-9afbde3815d04fad88840e127c2cdf89
Source dataset
uspto-grants-2010_10
Patent number
US07816523B2

Reaction notes

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