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

HRID 1976272Notes

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.[OH-:22].[Na+]>O>[OH:22][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

Conditions

Temperature: 20 °C

Procedure

50 g (0.118 mol of 3(R,S)-bromo-1-methyl4-(2,4,6-trimethoxyphenyl)-1,2,3,6-tetrahydropyridine hydrobromide (VI) were heated under reflux for 2 h in 100 ml of water. The reaction mixture was then cooled to 20° C. and adjusted to pH 12.5 by dropwise addition of 30 ml of 30% strength sodium hydroxide solution. After a short time, a pale brown precipitate crystallized out. The mixture was stirred at 5-10° C. for a further 1 h, and the precipitated product was filtered off with suction and washed with 30 ml of water. The crude product was then stirred with 20 ml of acetone, filtered off with suction and dried in vacuo.

Workup

customAfter a short time, a pale brown precipitate crystallized out
filtrationthe precipitated product was filtered off with suction
washwashed with 30 ml of water
stirringThe crude product was then stirred with 20 ml of acetone
filtrationfiltered off with suction
customdried in vacuo

Sources & evidence

ORD record: ord-f8b7f93710434a328b0039240fa46cef
Source dataset: uspto-grants-2001_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06225473B1

Reaction notes

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