Water → HCID 70580258, compound

HRID 904151Notes

Reaction equation

HRID 904151 reaction equation
B(Br)(Br)Br.[NH:5]1[CH:9]=[CH:8][N:7]=[C:6]1[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17]C)=[CH:13][N:12]=1.C1(N)C(F)=C(F)C(F)=C(N)C=1F.Cl.Cl.O>C(Cl)Cl>[NH:5]1[CH:9]=[CH:8][N:7]=[C:6]1[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][N:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 25134Boron tribromideHCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 70581241HCID 70581241, compound

Product 1

HCID 70580258HCID 70580258, compoundYield 342.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Boron tribromide (1.0 ml) was added dropwise to a stirred solution of 2-(1-imidazolylmethyl)-5-methoxy-pyridine (0.0378 g.) (prepared similarly to Example 18 but without converting the end product to the dihydrochloride) in dry methylene chloride (20 ml) at -70° and the resulting mixture was stirred at -70° for 30 minutes, and then at room temperature for 3 hours. Water was then added and the layers were separated. The aqueous layer was made just alkaline with solid sodium bicarbonate and evaporated to dryness. The residue was extracted several times with hot ethyl acetate and the combined extracts were filtered and evaporated until crystallisation commenced. The mixture was allowed to cool and the solid was filtered off to give 2-(1-imidazolylmethyl)-5-hydroxypyridine (0.120 g), m.p. 149°-151°.

Workup

  1. customprepared similarly to Example 18
  2. customat -70°
  3. waitat room temperature for 3 hours
  4. customthe layers were separated
  5. customevaporated to dryness
  6. extractionThe residue was extracted several times with hot ethyl acetate
  7. filtrationthe combined extracts were filtered
  8. customevaporated until crystallisation
  9. temperatureto cool
  10. filtrationthe solid was filtered off

Sources & evidence

ORD record
ord-00640d4836c04af880a9172433ae56f3
Source dataset
uspto-grants-1980_10
Patent number
US04230714

Reaction notes

Loading…