HCID 67981010, compound → HCID 67980853, compound

HRID 2173802Notes

Reaction equation

HRID 2173802 reaction equation
[OH:1][CH:2]([C:7]1[CH:16]=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][N:8]=1)[CH2:3][CH:4]([CH3:6])[CH3:5]>ClCCl.[O-2].[O-2].[Mn+4]>[CH3:5][CH:4]([CH3:6])[CH2:3][C:2]([C:7]1[CH:16]=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][N:8]=1)=[O:1]

Participants

4

Reactant 1

HCID 67981010HCID 67981010, compound

Product 1

HCID 67980853HCID 67980853, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 6-(1-hydroxy-3-methylbutyl)nicotinate (0.200 g, 0.896 mmol) in dichloromethane (10 mL) was added manganese dioxide (779 mg, 8.96 mmol). The reaction was stirred at room temperature overnight. The reaction was then filtered and concentration of the filtrate gave methyl 6-(3-methylbutanoyl)nicotinate (190 mg, 96%) as a yellow oil. 1H NMR (400 MHz, CDCl3, δ): 9.25 (s, 1H), 8.40-8.42 (d, 1H), 8.07-8.09 (d, 1H), 3.98 (s, 3H), 3.11-3.12 (d, 2H), 2.27-2.34 (m, 1H), 0.99-1.00 (m, 6H).

Workup

  1. filtrationThe reaction was then filtered

Sources & evidence

ORD record
ord-179d6f36f8cf41d0abe37d22f903626c
Source dataset
uspto-grants-2015_06
Patent number
US09056834B2

Reaction notes

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