3,4-Dichloroaniline → Methyl 5-(3,4-dichlorophenylamino)pyrazine-2-carboxylate

HRID 77472Notes

Reaction equation

HRID 77472 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[Cl:9])[NH2:5].Cl[C:11]1[N:12]=[CH:13][C:14]([C:17]([O:19][CH3:20])=[O:18])=[N:15][CH:16]=1>O1CCOCC1>[Cl:1][C:2]1[CH:3]=[C:4]([NH:5][C:11]2[N:12]=[CH:13][C:14]([C:17]([O:19][CH3:20])=[O:18])=[N:15][CH:16]=2)[CH:6]=[CH:7][C:8]=1[Cl:9]

Participants

4

Reactant 2

HCID 72573,4-DichloroanilineHCID 406081Methyl 5-chloropyrazine-2-carboxylate

Product 1

HCID 86679761Methyl 5-(3,4-dichlorophenylamino)pyrazine-2-carboxylateYield 51.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 3,4-dichloroaniline (1.127 g, 6.95 mmol) and methyl 5-chloropyrazine-2-carboxylate (0.6 g, 3.48 mmol) in dioxane (32 mL) was heated at 100° C. for 7 days, then cooled to room temperature and concentrated. The residue was triturated with methanol and filtered. The brown filter cake was washed with methanol and dried to yield methyl 5-(3,4-dichlorophenylamino)pyrazine-2-carboxylate (0.53 g, 51%). 1H NMR (400 MHz, DMSO-d6) δ ppm 10.44 (1H, s), 8.81 (1H, d, J=1.26 Hz), 8.30 (1H, d, J=1.51 Hz), 8.21 (1H, d, J=2.26 Hz), 7.46-7.73 (2H, m), 3.58 (2H, s). LCMS: R.T.=4.07; [M+H]+=298.12.

Workup

  1. temperaturecooled to room temperature
  2. concentrationconcentrated
  3. customThe residue was triturated with methanol
  4. filtrationfiltered
  5. washThe brown filter cake was washed with methanol
  6. customdried

Sources & evidence

ORD record
ord-e1a31e7fa8f345a8b0fbe839f635251e
Source dataset
uspto-grants-2014_09
Patent number
US08841301B2

Reaction notes

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