6-Aminonicotinic acid → Methyl 6-aminonicotinate

HRID 381732Notes

Reaction equation

HRID 381732 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=1.[CH3:11][Si](C=[N+]=[N-])(C)C>CO.CC#N.C(Cl)Cl>[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH3:11])=[O:7])=[CH:4][N:3]=1

Participants

6

Reactant 2

HCID 184966-Aminonicotinic acidHCID 167693Trimethylsilyldiazomethane

Product 1

HCID 737487Methyl 6-aminonicotinate

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

To a suspension of 6-aminonicotinic acid (1.00 g, 7.24 mmol) in MeOH (20 ml) and MeCN (10 ml) was added 10% solution of trimethylsilyldiazomethane in CH2Cl2 (25 ml) at room temperature. After stirring at room temperature for 0.5 h, the solvent was evaporated to give crude methyl 6aminonicotinate as a yellow solid. Title compound was prepared from this crude methyl 6-aminonicotinate in 17% yield according to a procedure similar to that described in Preparation 6.

Workup

  1. customthe solvent was evaporated

Sources & evidence

ORD record
ord-2406e9ed083843aebc0dffc2ebd571a2
Source dataset
uspto-grants-2001_10
Patent number
US06307061B2

Reaction notes

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