Methanol → HCID 13952723, compound

HRID 2058186Notes

Reaction equation

HRID 2058186 reaction equation
Cl[C:2]1[N:11]=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].CO.[CH2:14]([NH2:16])[CH3:15].[NH4+].[OH-]>O>[CH2:14]([NH:16][C:2]1[N:11]=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5])[CH3:15]

Participants

6

Reactant 4

HCID 887Methanol2×HCID 6341EthylamineHCID 14923Ammonium HydroxideHCID 819931Methyl 2-chloronicotinate

Product 1

HCID 13952723HCID 13952723, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 10 g. (0.06 mole) of methyl 2-chloronicotinate in 50 ml. of methanol was added 6.0 g. (0.13 mole) of ethylamine in 25 ml. of methanol and this was placed into an autoclave and heated on a steam bath for 4 hours. Then the reaction solution was stripped, water added, made very basic via NH4OH, extracted into CHCl3, washed with water, dried and then stripped to dryness to yield 2-ethylaminonicotinic acid, methyl ester. An HCl-salt was prepared by adding the crude residue to ethyl acetate and then adding ethereal-HCl. The product precipitated out of solution and was collected on a filter and rinsed with petroleum ether to give 7 g. of product with a m.p. of 140°-5° C.

Workup

  1. temperatureheated on a steam bath for 4 hours
  2. extractionextracted into CHCl3
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-5d87ef9447304f00b31fcb852a6916b8
Source dataset
uspto-grants-1980_07
Patent number
US04215123

Reaction notes

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