Hydrochloric Acid → (3-Amino-6-chloropyridin-2-yl)methanol

HRID 475327Notes

Reaction equation

HRID 475327 reaction equation
[NH2:1][C:2]1[C:3]([C:9](O)=[O:10])=[N:4][C:5]([Cl:8])=[CH:6][CH:7]=1.B.C1COCC1.Cl.C([O-])(O)=O.[Na+]>C1COCC1.O>[NH2:1][C:2]1[C:3]([CH2:9][OH:10])=[N:4][C:5]([Cl:8])=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 2723981Borane;tetrahydrofuranHCID 533934343-Amino-6-chloropyridine-2-carboxylic acid

Product 1

HCID 19353056(3-Amino-6-chloropyridin-2-yl)methanol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

3-amino-6-chloro-pyridine-2-carboxylic acid (95 mg, 0.55 mmol) is taken up in THF (1 mL) and combined with BH3-THF complex (2.2 mL, 2.2 mmol, 1 M in THF). The reaction mixture is stirred for 2 d at 20° C. The reaction is ended with dilute HCl and H2O, then neutralised with NaHCO3, extracted with EtOAc, the organic phase is dried on MgSO4, the solvent is eliminated in vacuo and (3-amino-6-chloro-pyridin-2-yl)-methanol is obtained (HPLC-MS: tRet.=0.79 min, MS(M+H)+=159; method AFEC).

Workup

  1. extractionextracted with EtOAc
  2. customthe organic phase is dried on MgSO4

Sources & evidence

ORD record
ord-af812f5ad6794187ae9e247e4dfa5dae
Source dataset
uspto-grants-2014_01
Patent number
US08637549B2

Reaction notes

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