Lithium borohydride → (6-Chloro-4-(methylamino)pyridin-3-yl)methanol

HRID 2404033Notes

Reaction equation

HRID 2404033 reaction equation
[Cl:1][C:2]1[CH:12]=[C:11]([NH:13][CH3:14])[C:5]([C:6](OCC)=[O:7])=[CH:4][N:3]=1.[BH4-].[Li+]>C1COCC1.CO>[Cl:1][C:2]1[N:3]=[CH:4][C:5]([CH2:6][OH:7])=[C:11]([NH:13][CH3:14])[CH:12]=1

Participants

5

Reactant 2

HCID 4148881Lithium borohydrideHCID 20627001Ethyl 6-chloro-4-(methylamino)pyridine-3-carboxylate

Product 1

HCID 51000240(6-Chloro-4-(methylamino)pyridin-3-yl)methanolYield 111.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
55 °C

Procedure

To a solution of ethyl 6-chloro-4-(methylamino)nicotinate (4.7 g, 21.9 mmol) in THF (30 mL) and methanol (30 mL) was added lithium borohydride (2.4 g, 109.8 mmol), and the reaction mixture was heated at 55° C. overnight. LCMS showed the reaction was completed. The reaction was cooled to RT, quenched with water (1 mL) and filtered. The filtrate was concentrated to afford the title compound (4.2 g, crude) as a white solid, which was directly used in the next step without further purification. MS (ES+) C7H9ClN2O requires: 172, 174. found: 173, 175 [M+H]+.

Workup

  1. temperatureThe reaction was cooled to RT
  2. customquenched with water (1 mL)
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-1d3a6bf26b87445aa787222a05977462
Source dataset
uspto-grants-2014_08
Patent number
US08802697B2

Reaction notes

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