Ammonia → HCID 12905278, compound

HRID 372208Notes

Reaction equation

HRID 372208 reaction equation
[CH3:1][O:2][C:3]1[N:11]=[C:10]([Cl:12])[CH:9]=[CH:8][C:4]=1[C:5](Cl)=[O:6].[CH2:13]([N:15]1[CH2:19][CH2:18][CH2:17][CH:16]1[CH2:20][NH2:21])[CH3:14].N>C(Cl)(Cl)Cl.C1C=CC=CC=1>[CH2:13]([N:15]1[CH2:19][CH2:18][CH2:17][CH:16]1[CH2:20][NH:21][C:5](=[O:6])[C:4]1[CH:8]=[CH:9][C:10]([Cl:12])=[N:11][C:3]=1[O:2][CH3:1])[CH3:14]

Participants

6

Reactant 3

HCID 222AmmoniaHCID 1172952-Aminomethyl-1-ethylpyrrolidineHCID 203287966-Chloro-2-methoxy-3-pyridinecarbonyl chloride

Product 1

HCID 12905278HCID 12905278, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 6212ChloroformSolvent

Conditions

Temperature
50 °C

Procedure

5.02 g (0.025 mole) of crude 2-methoxy-6-chloronicotinoyl chloride are dissolved in 75 ml of absolute chloroform and the solution is added dropwise in the course of 30 minutes at 25°-30° C to a solution of 7.7 g (0.06 mole) of 1-ethyl-2-(aminomethyl)-pyrrolidine in 75 ml of absolute benzene. The reaction mixture is stirred for 3 hours at 50° C, cooled, and 10 ml of a 5 N ethanolic ammonia solution are added thereto. The organic solvents are evaporated in vacuo and the residual crude base is chromatographed through a column of basic silica gel with benzene which contains 0.5% of methanol. Pure N-[(1-ethyl-2-pyrrolidinyl)-methyl]-2-methoxy-6-chloronicotinamide is obtained as an oil.

Workup

  1. temperaturecooled
  2. customThe organic solvents are evaporated in vacuo
  3. customthe residual crude base is chromatographed through a column of basic silica gel with benzene which

Sources & evidence

ORD record
ord-2167f23501184e8faf3a54b85ce16017
Source dataset
uspto-grants-1978_05
Patent number
US04089960

Reaction notes

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