Ethyl Acetate → 2-(6-Aminopyridin-3-yl)propan-2-ol

HRID 600629Notes

Reaction equation

HRID 600629 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:5](C(OC)=O)=[CH:4][N:3]=1.[CH3:12][Mg]Cl.[Cl-].[NH4+].C([O:20][CH2:21][CH3:22])(=O)C>C1COCC1>[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C:21]([OH:20])([CH3:22])[CH3:12])=[CH:10][CH:11]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 737487Methyl 6-aminonicotinateHCID 178418332HCID 178418332, compound

Product 1

HCID 594737712-(6-Aminopyridin-3-yl)propan-2-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 0.7 g of methyl 6-aminonicotinate in 65 mL of THF, cooled to 10° C. and under argon, are added dropwise 15 mL of a 3M solution of methylmagnesium chloride in THF. The reaction mixture is stirred for 15 hours, while allowing the temperature to rise to 20° C., and is then cooled again in an ice bath. 100 mL of saturated ammonium chloride solution and then 200 mL of ethyl acetate are added slowly. The organic phase is dried and concentrated to dryness. The residue is taken up in ethyl acetate. The precipitate is filtered off by suction and dried to give 0.4 g of 2-(6-aminopyridin-3-yl)propan-2-ol in the form of a pale yellow solid.

Workup

  1. customto rise to 20° C.
  2. temperatureis then cooled again in an ice bath
  3. customThe organic phase is dried
  4. concentrationconcentrated to dryness
  5. filtrationThe precipitate is filtered off by suction
  6. customdried

Sources & evidence

ORD record
ord-13ab20eb2c00429ab4850ab6beff6d24
Source dataset
uspto-grants-2011_03
Patent number
US07902219B2

Reaction notes

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