Acetic Acid → HCID 3999190, compound

HRID 2231161Notes

Reaction equation

HRID 2231161 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[CH:12][N:11]=2)[CH:5]=[CH:6][C:7]=1[O:8]C.Br.C(O)(=O)C>O>[F:1][C:2]1[CH:3]=[C:4]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[CH:12][N:11]=2)[CH:5]=[CH:6][C:7]=1[OH:8]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 14069873HCID 14069873, compound

Product 1

HCID 3999190HCID 3999190, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-(m-Fluoro-p-methoxyphenyl)-5-heptylpyridine (X) (13 g, 0.043 mol) obtained at the step (III) hydrobromic acid (47%) (50 ml) and acetic acid (140 ml) were heated under reflux for 30 hours, followed by cooling the reaction fluid, pouring it in water, filtering off the resulting crystals, dissolving the crystals in 2N-NaOH aqueous solution (about 100 ml), further adding acetic acid (30 ml) to obtain an acidic solution filtering off deposited crystals and recrystallizing them from ethyl alcohol to obtain 2-(m-fluoro-p-hydroxyphenyl)-5-heptylpyridine (a compound of the formula (XI) wherein X=f and R1 =C7H15) (7.2 g) having a m.p. of 83.7°-86.1° C.

Workup

  1. temperaturewere heated
  2. temperatureunder reflux for 30 hours
  3. temperatureby cooling
  4. customthe reaction fluid
  5. filtrationfiltering off the resulting crystals
  6. dissolutiondissolving the crystals in 2N-NaOH aqueous solution (about 100 ml), further adding acetic acid (30 ml)
  7. customto obtain an acidic solution
  8. filtrationfiltering off
  9. customrecrystallizing them from ethyl alcohol

Sources & evidence

ORD record
ord-90675db99f964a70a8677d8efcfcb627
Source dataset
uspto-grants-1988_11
Patent number
US04781857

Reaction notes

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