Pyridine → HCID 58860779, compound

HRID 1350055Notes

Reaction equation

HRID 1350055 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:13])[C:5]1[CH:10]=[C:9]([NH2:11])[CH:8]=[CH:7][C:6]=1[Cl:12].N1C=CC=CC=1.[C:20]1([O:26][C:27](Cl)=[O:28])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C1COCC1.C(OC(=O)C)C>[CH3:2][O:3][C:4](=[O:13])[C:5]1[CH:10]=[C:9]([NH:11][C:27]([O:26][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:28])[CH:8]=[CH:7][C:6]=1[Cl:12]

Participants

6

Reactant 3

HCID 1049PyridineHCID 15891Phenyl chloroformateHCID 25067350HCID 25067350, compound

Product 1

HCID 58860779HCID 58860779, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred mixture of 5-amino-2-chloro-benzoic acid methyl ester hydrochloride (1.110 g, 5.0 mmol) and pyridine (0.79 g, 10.0 mmol) in anhydrous THF (15 mL) at 0° C. was added phenylchloroformate (0.95 g, 6.0 mmol). After warming to room temperature, the reaction mixture was diluted with ethylacetate (50 mL), washed sequentially with 10% HCl, water and brine and dried over sodium sulfate. Removal of solvent under vacuum and purification of the product by flash chromatography (10% ethyl acetate in hexanes) yielded 0.8 g (53%) of a colorless solid. 1H NMR (300 MHz, DMSO-d6) δ3.9 (s, 3H), 7.0 (br s, 1H), 7.18 (m, 2H), 7.4 (m, 3H), 7.6 (m, 1H), 7.9 (d, J=2.5 Hz, 1H). Mass Spectrum (M−H): 3:1 ratio of 304 and 306.

Workup

  1. washwashed sequentially with 10% HCl, water and brine
  2. dry with materialdried over sodium sulfate
  3. customRemoval of solvent
  4. customunder vacuum and purification of the product by flash chromatography (10% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-0088c3217b68449e95695f757bd89353
Source dataset
uspto-grants-2007_05
Patent number
US07214677B2

Reaction notes

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