Diethyl Ether → Methyl 5-aminopyridine-2-carboxylate

HRID 2065565Notes

Reaction equation

HRID 2065565 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([OH:10])=[O:9])=[N:6][CH:7]=1.[CH3:11][Si](C=[N+]=[N-])(C)C.CCOCC>C1C=CC=CC=1.CO>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([O:10][CH3:11])=[O:9])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 167693TrimethylsilyldiazomethaneHCID 41797265-Aminopyridine-2-carboxylic acid

Product 1

HCID 12457877Methyl 5-aminopyridine-2-carboxylate

Reagents, catalysts & solvents 1

HCID 21927730Benzene methanolSolvent

Conditions

Temperature
0 °C

Procedure

5-Amino-pyridine-2-carboxylic acid 1 (5.4 mmol) is dissolved in benzene:MeOH 3:1 (40 mL) and cooled in an ice-bath to 0° C. To the solution is slowly added 2M TMSCH2N2 in Et2O solution (6.5 mmol). After the addition is complete, the reaction mixture is warmed to it and stirred for 6 h. After removing the solvent in vacuum, methyl 5-aminopicolinate 2 is obtained and used in the next step without further purification. MS (m/z) (M+1)+: 153.1.

Workup

  1. additionAfter the addition
  2. temperaturethe reaction mixture is warmed to it
  3. customAfter removing the solvent in vacuum

Sources & evidence

ORD record
ord-acbe7153b961483f959434d93fe27ae3
Source dataset
uspto-grants-2012_10
Patent number
US08288540B2

Reaction notes

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