5,6-Dichloronicotinic acid → (5,6-Dichloropyridin-3-yl)methanol

HRID 1582629Notes

Reaction equation

HRID 1582629 reaction equation
B.O1CCCC1.[Cl:7][C:8]1[C:9]([Cl:17])=[N:10][CH:11]=[C:12]([CH:16]=1)[C:13](O)=[O:14]>O1CCCC1>[Cl:17][C:9]1[C:8]([Cl:7])=[CH:16][C:12]([CH2:13][OH:14])=[CH:11][N:10]=1

Participants

4

Reactant 2

HCID 2479875,6-Dichloronicotinic acidHCID 2723981Borane;tetrahydrofuran

Product 1

HCID 21882961(5,6-Dichloropyridin-3-yl)methanolYield 45%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Borane-tetrahydrofuran complex (1M solution in tetrahydrofuran, 52 ml) was added to a stirred solution of 5,6-dichloronicotinic acid (2 g) in tetrahydrofuran (60 ml) over 20 minutes at 0° C. The reaction mixture was allowed to warm to room temperature over 90 minutes and then cooled to 0° C. and quenched with water (100 ml). The solution was saturated with solid sodium chloride and extracted with ethyl acetate and the combined organic extracts were dried and concentrated in vacuo. The residue was triturated with dichloromethane-50% ethyl acetate and the solid by-product was removed by filtration. The filtrate was concentrated in vacuo and purified by column chromatography using isohexane/ethyl acetate (1:1 v/v) as eluent to yield the product as a white solid (820 mg, 45%). NMR: δ 4.55 (d, 2H), 5.5 (t, 1H), 8.0 (m, 1H), 8.3 (m, 1H); m/z 178.1 (M+H+).

Workup

  1. temperaturecooled to 0° C.
  2. customquenched with water (100 ml)
  3. extractionextracted with ethyl acetate
  4. customthe combined organic extracts were dried
  5. concentrationconcentrated in vacuo
  6. customThe residue was triturated with dichloromethane-50% ethyl acetate
  7. customthe solid by-product was removed by filtration
  8. concentrationThe filtrate was concentrated in vacuo
  9. custompurified by column chromatography

Sources & evidence

ORD record
ord-93d3a2f7eabb4d299df540e11a5b3686
Source dataset
uspto-grants-2004_05
Patent number
US06737435B1

Reaction notes

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