Ammonia → HCID 178428602, compound

HRID 1753763Notes

Reaction equation

HRID 1753763 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([OH:8])[CH:3]=1.CCOC(C)=O.C1C(=O)N([Br:22])C(=O)C1.N>C(O)(=O)C>[Br:22][C:3]1[C:4]([OH:8])=[N:5][CH:6]=[CH:7][C:2]=1[CH3:1]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 8857Ethyl AcetateHCID 67184N-bromobutanimideHCID 178428601HCID 178428601, compound

Product 1

HCID 178428602HCID 178428602, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 4-methyl-pyridin-2-ol V-a (25 g, 229 mmol) in glacial acetic acid (350 mL) and EtOAc (680 mL) was treated with NBS (37.4 g, 210 mmol) and stirred at room temperature for 30 min. The mixture was then taken to pH 8 with aqueous ammonia and extracted with EtOAc. The separated organics were washed with 1:1 H2O/brine then dried (MgSO4), filtered and evaporated before purification by silica column chromatography (1-4% EtOH/DCM) to afford the desired product V-b as a white solid (8.66 g). 1H NMR (300 MHz, DMSO) δ 11.90 (s, 1H), 7.32 (d, J=6.6 Hz, 1H), 6.19 (d, J=6.6 Hz, 1H), 2.25 (s, 3H).

Workup

  1. extractionextracted with EtOAc
  2. washThe separated organics were washed with 1:1 H2O/brine
  3. dry with materialthen dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated before purification by silica column chromatography (1-4% EtOH/DCM)

Sources & evidence

ORD record
ord-6eca0fb214a14411b177f14ee5915f67
Source dataset
uspto-grants-2015_10
Patent number
US09168245B2

Reaction notes

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