Acetyl chloride → Methyl 2-amino-6-methylisonicotinate

HRID 402463Notes

Reaction equation

HRID 402463 reaction equation
[C:1](Cl)(=O)C.[NH2:5][C:6]1[CH:7]=[C:8]([CH:12]=[C:13]([CH3:15])[N:14]=1)[C:9]([OH:11])=[O:10]>CO>[CH3:1][O:10][C:9](=[O:11])[C:8]1[CH:12]=[C:13]([CH3:15])[N:14]=[C:6]([NH2:5])[CH:7]=1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 124040272-Amino-6-methylisonicotinic acid

Product 1

HCID 53420312Methyl 2-amino-6-methylisonicotinate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To 50 ml of MeOH is added drop wise acetyl chloride (3 ml) at room temperature. After 15 min, 2-amino-6-methylisonicotinic acid (2.3 g) is added and the mixture is stirred overnight at 50° C. After concentrating the solution, the resulting residue is suspended in acetone and then filtered and dried at 50° C. in vacuum, to yield 2-amino-6-methylisonicotinic acid methyl ester (4.1 g). HPLC: Rt=0.91 min (method D)

Workup

  1. concentrationAfter concentrating the solution
  2. filtrationfiltered
  3. customdried at 50° C. in vacuum

Sources & evidence

ORD record
ord-1a62b0fd9eb045408965980ca81f6370
Source dataset
uspto-grants-2014_06
Patent number
US08742115B2

Reaction notes

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