Ammonia → (3,4-Dimethylpyridin-2-yl)(3,4,5-trimethoxyphenyl)methanol

HRID 1974310Notes

Reaction equation

Br[C:2]1[C:7]([CH3:8])=[C:6]([CH3:9])[CH:5]=[CH:4][N:3]=1.C([Li])CCC.[CH3:15][O:16][C:17]1[CH:18]=[C:19]([CH:22]=[C:23]([O:27][CH3:28])[C:24]=1[O:25][CH3:26])[CH:20]=[O:21].Cl.N>CCOCC.C1C=CC=CC=1>[CH3:28][O:27][C:23]1[CH:22]=[C:19]([CH:20]([C:2]2[C:7]([CH3:8])=[C:6]([CH3:9])[CH:5]=[CH:4][N:3]=2)[OH:21])[CH:18]=[C:17]([O:16][CH3:15])[C:24]=1[O:25][CH3:26]

Participants

Conditions

Temperature: -40 °C

Procedure

40 g of 2-bromo-3,4-dimethylpyridine dissolved in 50 ml of anhydrous ether are slowly added, with agitation and under a nitrogen atmosphere, to 300 ml of a 0.9 M solution of butyl-lithium in ether cooled to -40° C. The resulting mixture is agitated for 2 hours at this temperature, and 50 g of 3,4,5-trimethoxybenzaldehyde dissolved in 200 ml of anhydrous benzene are added, and the mixture kept at a temperature below -25° C. Agitation is performed for 1 hour at -15° C, and the reaction is continued until ambient temperature is reached. The mixture is poured on to ice and dilute hydrochloric acid, the acid layer is made alkaline with a current of ammonia, while cooling externally with ice. The precipitate is collected by filtration, supplying 62.6 g of (II). Yield 96%. An analysis sample is crystallized from alcohol (m.p. = 104-6° C). Analysis: C17H21NO4. Calculated: C = 67.31, H = 6.98, N = 4.62. Found: C = 67.23, H = 7.33, N = 4.57.

Workup

additionare added
customkept at a temperature below -25° C
customis continued until ambient temperature
temperaturewhile cooling externally with ice
filtrationThe precipitate is collected by filtration
customAn analysis sample is crystallized from alcohol (m.p. = 104-6° C)

Sources & evidence

ORD record: ord-1ba60369a52240a9a98f672284bfb9b7
Source dataset: uspto-grants-1976_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04000283

Reaction notes

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