Pyridine → 3-cyano-benzoic acid tert-butyl ester

HRID 628820Notes

Reaction equation

HRID 628820 reaction equation
[C:1]([OH:5])([CH3:4])([CH3:3])[CH3:2].N1C=CC=CC=1.[C:12]([C:14]1[CH:15]=[C:16]([CH:20]=[CH:21][CH:22]=1)[C:17](Cl)=[O:18])#[N:13]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[C:1]([O:5][C:17](=[O:18])[C:16]1[CH:20]=[CH:21][CH:22]=[C:14]([C:12]#[N:13])[CH:15]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 1049Pyridine2×HCID 6386tert-ButanolHCID 3084833-Cyanobenzoyl chloride

Product 1

HCID 111717003-cyano-benzoic acid tert-butyl esterYield 82.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

Part B. To a mixture of tert-butanol (3.50 g, 47.22 mmol), pyridine (3.72 g, 46.78 mmol) and cat. DMAP in methylene chloride (15 mL) is added dropwise 3-cyanobenzoyl chloride (6.81 g, 41.07 mmol) and pyridine (3 mL) in methylene chloride (10 mL) at 0° C. The resulting mixture is stirred at room temperature for 20 h. The solvent is evaporated, and the residue is purified by flash chromatography (1:1 methylene chloride/hexanes) to afford 3-cyano-benzoic acid tert-butyl ester (6.84 g, 82.1% yield) as white solid. 1H NMR (300 MHz, CDCl3): δ 8.24 (1H, s), 8.20 (1H, dd, J=7.9, 1.2 Hz), 7.78 (1H, dd, J=6.7, 1.1 Hz), 7.52 (1H, m), 1.58 (9H, s).

Workup

  1. customThe solvent is evaporated
  2. customthe residue is purified by flash chromatography (1:1 methylene chloride/hexanes)

Sources & evidence

ORD record
ord-00c3eb5c601d4709a1130f2fe4c37aa2
Source dataset
uspto-grants-2016_04
Patent number
US09315467B2

Reaction notes

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