Methylamine → HCID 63376437, compound

HRID 536282Notes

Reaction equation

HRID 536282 reaction equation
Cl[C:2]1[N:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].O1CCCC1.[CH3:17][NH2:18]>CO.CCOC(C)=O>[Cl:11][C:9]1[CH:8]=[CH:7][C:3]([C:4]([OH:6])=[O:5])=[C:2]([NH:18][CH3:17])[N:10]=1

Participants

6

Reactant 3

HCID 6329MethylamineHCID 8028TetrahydrofuranHCID 8540472,6-Dichloronicotinic acid

Product 1

HCID 63376437HCID 63376437, compoundYield 99.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

To a steel autoclave was added 2,6-dichloronicotinic acid (tech.) (30 g, 156.2 mmoles), tetrahydrofuran (30 mL) and monomethylamine (68.2 mL. 33 wt % in ethanol, 500 mmol). The reaction vessel was heated at 100° C. for 4 h. The reaction mixture was cooled and the solution transferred from the autoclave to a 500 mL flask and concentrated under vacuum to give a green solid. The solid was dissolved in 300 mL MeOH and 1.2 L EtOAc, poured into a separatory funnel and washed with 1N HCl (2×300 mL) and brine. The organic solution was then concentrated to dryness to yield 6-chloro-2-(methylamino)nicotinic acid (29 g, 96%) as an off-white solid.

Workup

  1. temperatureThe reaction mixture was cooled
  2. customthe solution transferred from the autoclave to a 500 mL flask
  3. concentrationconcentrated under vacuum
  4. customto give a green solid
  5. washwashed with 1N HCl (2×300 mL) and brine
  6. concentrationThe organic solution was then concentrated to dryness

Sources & evidence

ORD record
ord-a3e9b866d3b44a58a303f66dd588c9f5
Source dataset
uspto-grants-2014_10
Patent number
US08859577B2

Reaction notes

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