Sodium borohydride → HCID 12993694, compound

HRID 1837441Notes

Reaction equation

HRID 1837441 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[C:9]([Cl:10])=[C:8]([Cl:11])[N:7]=[C:6]([C:12](OC)=[O:13])[CH:5]=1>CO>[Cl:3][C:4]1[C:9]([Cl:10])=[C:8]([Cl:11])[N:7]=[C:6]([CH2:12][OH:13])[CH:5]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydride2×HCID 12993691Methyl 4,5,6-trichloropicolinate

Product 1

HCID 12993694HCID 12993694, compoundYield 80.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

Sodium borohydride (173 mg, 4.60 mmol) was added to a mixture of methyl 4,5,6-trichloropyridine-2-carboxylate (1.0 g, 4.16 mmol) in methanol (25 mL) at room temperature. After 40 min, the reaction was warmed to 50° C., and additional sodium borohydride (307 mg, 8 mmol) was added in 2 batches over the following 3 hours. The methanol was removed by rotary evaporation and the residue was diluted with 10% citric acid, aq. (50 mL) and stirred vigorously. The precipitate was collected, washed with water and dried to provide (4,5,6-trichloropyridin-2-yl)methanol (713 mg, 3.34 mmol), mp 82-83° C.

Workup

  1. customThe methanol was removed by rotary evaporation
  2. additionthe residue was diluted with 10% citric acid, aq. (50 mL)
  3. customThe precipitate was collected
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-ba0292b447da4fca8f34efd4c7d5f940
Source dataset
uspto-grants-2004_08
Patent number
US06784137B2

Reaction notes

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