Methylamine → HCID 83702359, compound

HRID 1055661Notes

Reaction equation

HRID 1055661 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:12]=[C:13](Cl)[N:14]=1)[C:8]([O:10]C)=[O:9])([CH3:4])([CH3:3])[CH3:2].[CH3:16][NH2:17]>>[C:1]([C:5]1[CH:6]=[C:7]([CH:12]=[C:13]([NH:17][CH3:16])[N:14]=1)[C:8]([OH:10])=[O:9])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 6329MethylamineHCID 86690963Methyl 2-chloro-6-(1,1-dimethylethyl)-4-pyridinecarboxylate

Product 1

HCID 83702359HCID 83702359, compound

Conditions

Temperature
130 °C

Procedure

1.0 g (4.39 mmol) of methyl 2-tert-butyl-6-chloroisonicotinate [lit.: O. Isler et al., Helvetica Chimica Acta 1955, 38 (4), 1033-1046] and 3.8 ml (43.9 mmol) of a 40% strength aqueous methylamine solution were heated in a microwave oven (Biotage Initiator, with Dynamic Field Tuning) at 160° C. for 6 h. After cooling, the volatile components were removed on a rotary evaporator. The residue was taken up in 4 ml of semiconcentrated hydrochloric acid and once more heated in the microwave at 130° C. for 1 h. The product was then isolated directly by preparative HPLC (Method 12). Evaporation of the product fractions and drying of the residue under high vacuum gave 180 mg (92% pure, 18% of theory) of the title compound.

Workup

  1. temperatureAfter cooling
  2. customthe volatile components were removed on a rotary evaporator
  3. customThe product was then isolated directly by preparative HPLC (Method 12)
  4. customEvaporation of the product fractions
  5. customdrying of the residue under high vacuum

Sources & evidence

ORD record
ord-82cd0cbe09a344a2bab0fa75633040ca
Source dataset
uspto-grants-2016_07
Patent number
US09394309B2

Reaction notes

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