Pyridine → Phenyl 6-methoxypyridin-3-ylcarbamate

HRID 1666334

Reaction equation

HRID 1666334 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6](OC)[CH:7]=1.N1C=CC=CC=1.[C:16]1([O:22][C:23](Cl)=[O:24])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C1C[O:29][CH2:28]C1>>[CH3:28][O:29][C:5]1[N:4]=[CH:3][C:2]([NH:1][C:23](=[O:24])[O:22][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:7][CH:6]=1

Participants

5

Reactant 4

HCID 1049PyridineHCID 8028TetrahydrofuranHCID 15891Phenyl chloroformateHCID 127035955-Methoxypyridin-3-ylamine

Product 1

HCID 20185962Phenyl 6-methoxypyridin-3-ylcarbamateYield 96%

Conditions

Temperature
0 °C

Procedure

3-Amino-5-methoxy-pyridine (5.00 g, 40.3 mmol) was dissolved in THF (80 mL), cooled to 0° C., treated with pyridine (4.07 mL, 50.4 mmol) followed by phenylchloroformate (5.32 mL, 42.3 mmol). The reaction mixture was slowly warmed to RT over several hours and stirred an additional 12 h. The mixture was partitioned between water and EtOAc. The organic layer was separated and the aqueous layer was extracted again. The combined organic extracts were dried over sodium sulfate, filtered and concentrated to give the product as a reddish solid (9.45 g, 96%), which was used without purification.

Workup

  1. temperatureThe reaction mixture was slowly warmed to RT over several hours
  2. customThe mixture was partitioned between water and EtOAc
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted again
  5. dry with materialThe combined organic extracts were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-bf15aa18ac8640bd9f5cd0e1d19e0ffa
Source dataset
uspto-grants-2011_10
Patent number
US08044052B2

Linked notes

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