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

HRID 645375Notes

Reaction equation

HRID 645375 reaction equation
[CH3:1][Mg]Cl.[NH2:4][C:5]1[CH:14]=[CH:13][C:8](C(OC)=O)=[CH:7][N:6]=1.[Cl-].[NH4+].C([O:20][CH2:21][CH3:22])(=O)C>C1COCC1>[NH2:4][C:5]1[N:6]=[CH:7][C:8]([C:21]([OH:20])([CH3:22])[CH3:1])=[CH:13][CH:14]=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

15 ml of a 3M solution of methylmagnesium chloride in THF are added dropwise to a solution, cooled to 10° C. and under argon, of 0.7 g of methyl 6-aminonicotinate in 65 ml of THF. The reaction mixture is stirred for 15 h, while allowing the temperature to rise to 20° C., and then again cooled in an ice bath. 100 ml of a saturated ammonium chloride solution and then 200 ml of ethyl acetate are slowly added. The organic phase is dried and concentrated to dryness. The residue is taken up in ethyl acetate. The precipitate is filtered off 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. temperatureagain cooled in an ice bath
  3. customThe organic phase is dried
  4. concentrationconcentrated to dryness
  5. filtrationThe precipitate is filtered off
  6. customdried

Sources & evidence

ORD record
ord-d9948faaa43a44b98bbd66fdba04ba95
Source dataset
uspto-grants-2010_04
Patent number
US07704989B2

Reaction notes

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