Borane → (6-Chloro-5-methoxypyridin-3-yl)methanol

HRID 1924853Notes

Reaction equation

HRID 1924853 reaction equation
[Cl:1][C:2]1[C:10]([O:11][CH3:12])=[CH:9][C:5]([C:6](O)=[O:7])=[CH:4][N:3]=1.B>C1COCC1>[Cl:1][C:2]1[N:3]=[CH:4][C:5]([CH2:6][OH:7])=[CH:9][C:10]=1[O:11][CH3:12]

Participants

4

Reactant 2

HCID 6331BoraneHCID 469118426-Chloro-5-methoxynicotinic acid

Product 1

HCID 59297074(6-Chloro-5-methoxypyridin-3-yl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 6-chloro-5-methoxynicotinic acid (0.54 g, 2.9 mmol) in THF (5 mL) at 25° C. was added borane (1.0 M in THF, 5.8 mL, 5.8 mmol) dropwise. The mixture was let stir for 5 h, after which TLC showed complete conversion. The reaction was quenched with 2 M HCl until bubbling subsided and mixture extracted with dichloromethane (3×). The combined organic layers were dried over MgSO4 and concentrated to furnish the product (6-chloro-5-methoxypyridin-3-yl)methanol as a white solid (0.49 mg (97%); mp 60-63° C.; 1H NMR (400 MHz, CDCl3) δ 7.95 (d, 1H), 7.30 (d, 1H), 4.74 (s, 2H), 3.94 (s, 3H): LC-MS (ELSD): Exact mass calcd for C7H8ClNO2 [M]+, 173. Found 173.

Workup

  1. customThe reaction was quenched with 2 M HCl
  2. customuntil bubbling
  3. extractionmixture extracted with dichloromethane (3×)
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-17c5237726c14866ae41f1e6cd689b0e
Source dataset
uspto-grants-2012_05
Patent number
US08178565B2

Reaction notes

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