Methylamine → 5-(METHYLAMINO)NICOTINIC ACID

HRID 370734Notes

Reaction equation

HRID 370734 reaction equation
[CH3:1][NH2:2].Br[C:4]1[CH:5]=[N:6][CH:7]=[C:8]([CH:12]=1)[C:9]([OH:11])=[O:10]>C(O)C.O>[CH3:1][NH:2][C:4]1[CH:5]=[N:6][CH:7]=[C:8]([CH:12]=1)[C:9]([OH:11])=[O:10]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 887075-Bromonicotinic acid

Product 1

HCID 20501035-(METHYLAMINO)NICOTINIC ACID

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

The intermediate methyl 5-methylamino-nicotinate has been obtained as follows: reaction of methylamine (40% in water) with 5-bromo-nicotinic acid in autoclave at 140° C. for seven hours gives 5-methylamino-nicotinic acid, m.p. 239°-242° C. from ethanol/water; this acid reacts with SOCl in methanol under reflux for seven hours to afford the ester (methyl 5-methylaminonicotinate; m.p. 113°-115° C., from petroleum ether.

Sources & evidence

ORD record
ord-acda068c83224b3d9a07b870b2b38800
Source dataset
uspto-grants-1985_07
Patent number
US04528296

Reaction notes

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