Hydrogen Bromide → HCID 136353513, compound

HRID 267228Notes

Reaction equation

HRID 267228 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([C:11]2([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([CH2:23][CH2:24][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[N:18]=3)OCCC[O:12]2)[CH:6]=[CH:7][C:8]=1[O:9]C.[BrH:31]>>[BrH:31].[C:25]1([CH2:24][CH2:23][C:19]2[N:18]=[C:17]([C:11]([C:5]3[CH:6]=[CH:7][C:8]([OH:9])=[C:3]([OH:2])[CH:4]=3)=[O:12])[CH:22]=[CH:21][CH:20]=2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

3

Reactant 2

HCID 260Hydrogen BromideHCID 21825363HCID 21825363, compound

Product 1

HCID 136353513HCID 136353513, compound

Procedure

A solution of 3.5 g. of 2-(3,4-dimethoxyphenyl)-2-(6-phenylethyl-2-pyridyl)-1,3-dioxane in 20 ml. of 48% hydrobromic acid was heated under reflux for 20 hours. The solvent was removed under reduced pressure and industrial methylated spirit was evaporated several times from the residue which crystallized upon trituration with ethyl acetate. Recrystallization from methanolethyl acetate yielded (3,4-dihydroxyphenyl) (6-phenylethyl-2-pyridyl) ketone hydrobromide, m.p. 181°C. Analysis: Calculated for C20H18NO3Br: C, 60.0; H, 4.5; N, 3.5; Br, 20.0. Found: C, 60.2; H, 4.7; N, 3.6; Br, 20.35.

Workup

  1. temperatureunder reflux for 20 hours
  2. customThe solvent was removed under reduced pressure and industrial methylated spirit
  3. customwas evaporated several times from the residue which
  4. customcrystallized upon trituration with ethyl acetate
  5. customRecrystallization from methanolethyl acetate

Sources & evidence

ORD record
ord-d2e16b6302954b77830a0739d64cea3f
Source dataset
uspto-grants-1976_03
Patent number
US03941796

Reaction notes

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