Dichloroacetic Acid → 3-Chloro-4-hydroxy-6-methyl-1-(2-propen-1-yl)-2(1H)-pyridinone

HRID 1867047Notes

Reaction equation

HRID 1867047 reaction equation
[CH2:1]([N:4]1[C:9]([CH3:10])=[CH:8][C:7]([OH:11])=[CH:6][C:5]1=[O:12])[CH:2]=[CH2:3].C1C(=O)N(Br)C(=O)C1.[Cl:21]C(Cl)C(O)=O>CC#N>[CH2:1]([N:4]1[C:9]([CH3:10])=[CH:8][C:7]([OH:11])=[C:6]([Cl:21])[C:5]1=[O:12])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 6597Dichloroacetic AcidHCID 67184N-bromobutanimideHCID 54687827HCID 54687827, compound

Product 1

HCID 547241693-Chloro-4-hydroxy-6-methyl-1-(2-propen-1-yl)-2(1H)-pyridinoneYield 59%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 1-allyl-4-hydroxy-6-methylpyridin-2(1H)-one (500 mg, 3.0 mmol) in CH3CN (10 ml), at rt, was added sequentially n-bromosuccinimide (440 mg, 3.3 mmol) and dichloroacetic acid (546 μl, 6.62 mmol). The resulting mixture was stirred for 2 h. The heterogeneous mixture was filtered and the solid was washed with additional CH3CN to give 350 mg (59%) of the desired product as a tan solid. 1H-NMR (DMSOd6/300 MHz) δ 11.16 (s, 1H), 5.98-5.86 (m, 2H), 5.12 (dd, J=10.5, 1.5 Hz, 1H), 4.89 (dd, J=17.1, 1.5 Hz, 1H), 4.63-4.61 (m, 2H), 2.29 (s, 3H). ES-HRMS m/z 200.050 (M+H calcd for C9H11ClNO2=200.0470)

Workup

  1. filtrationThe heterogeneous mixture was filtered
  2. washthe solid was washed with additional CH3CN

Sources & evidence

ORD record
ord-1643d4b5006e452592e5a5e246510f20
Source dataset
uspto-grants-2009_12
Patent number
US07629363B2

Reaction notes

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