Pyridine → HCID 18979187, compound

HRID 2393192Notes

Reaction equation

HRID 2393192 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([C:18]2[C:19](=[O:30])[C:20]3[C:25]([C:26](=[O:29])[C:27]=2[CH3:28])=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:10][CH2:11][CH2:12][CH2:13][C:14]([NH:16][OH:17])=[O:15])=[CH:5][CH:4]=1.N1C=CC=CC=1.[C:37](OC(=O)C)(=[O:39])[CH3:38]>C1COCC1.CCOCC>[C:37]([O:17][NH:16][C:14](=[O:15])[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]([C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=1)[C:18]1[C:19](=[O:30])[C:20]2[C:25]([C:26](=[O:29])[C:27]=1[CH3:28])=[CH:24][CH:23]=[CH:22][CH:21]=2)(=[O:39])[CH3:38]

Participants

6

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 9822660HCID 9822660, compound

Product 1

HCID 18979187HCID 18979187, compoundYield 63.2%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

6-(4-Methoxyphenyl)-6-(3-methyl-1,4-naphthoquinon-2-yl)hexanohydroxamic acid (215 mg) and pyridine (125 mg) were dissolved in THF (1 ml) followed by addition of acetic anhydride (56 mg), and the mixture was stirred at room temperature for 2 hours. This reaction mixture was diluted with ether, washed serially with 1N HCl, saturated aqueous NaCl solution, and saturated aqueous NaHCO3 solution, dried, and concentrated under reduced pressure. The residue was applied to a silica gel column and developed with hexane-ethyl acetate (1:1) to provide the title compound (150 mg).

Workup

  1. washwashed serially with 1N HCl, saturated aqueous NaCl solution, and saturated aqueous NaHCO3 solution
  2. customdried
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2143ca345d614f6096d9a44cb4d866de
Source dataset
uspto-grants-1998_09
Patent number
US05804601

Reaction notes

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