Dichloromethane → 1,2,3,6-Tetrahydro-1-methyl-4-(2,4,6-trimethoxyphenyl)-3-pyridinol

HRID 2304802Notes

Reaction equation

HRID 2304802 reaction equation
Br.Br[CH:3]1[C:8]([C:9]2[C:14]([O:15][CH3:16])=[CH:13][C:12]([O:17][CH3:18])=[CH:11][C:10]=2[O:19][CH3:20])=[CH:7][CH2:6][N:5]([CH3:21])[CH2:4]1.C([O:26]C)(C)(C)C.ClCCl>O>[OH:26][CH:3]1[C:8]([C:9]2[C:14]([O:15][CH3:16])=[CH:13][C:12]([O:17][CH3:18])=[CH:11][C:10]=2[O:19][CH3:20])=[CH:7][CH2:6][N:5]([CH3:21])[CH2:4]1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 15413tert-Butyl methyl etherHCID 9866952HCID 9866952, compound

Product 1

HCID 99256571,2,3,6-Tetrahydro-1-methyl-4-(2,4,6-trimethoxyphenyl)-3-pyridinol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

first isolating the compound (VI) as a solid by stirring the reaction solution into a suitable organic solvent, methyl tert-butyl ether, dichloromethane etc., and subsequently reacting the resulting product with water and by stirring at 50°-100° C., preferably at 60°-80° C., to give 3(R,S)-hydroxy-1-methyl-4-(2,4,6-trimethoxyphenyl)-1,2,3,6-tetrahydropyridine (VII)

Sources & evidence

ORD record
ord-c4fe3fb1d9eb4f5ea1c4f46c38a6e2ce
Source dataset
uspto-grants-2002_08
Patent number
US06437136B1

Reaction notes

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