Ammonia → HCID 66799491, compound

HRID 2172731Notes

Reaction equation

HRID 2172731 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]3[N:19]=[C:18]([C:20]([O:22]C)=O)[CH:17]=[C:16]([CH:24]=[CH2:25])[CH:15]=3)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[NH3:26]>CO.C(Cl)(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]3[N:19]=[C:18]([C:20]([NH2:26])=[O:22])[CH:17]=[C:16]([CH:24]=[CH2:25])[CH:15]=3)=[CH:10][CH:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 66799651HCID 66799651, compound

Product 1

HCID 66799491HCID 66799491, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6212ChloroformSolvent

Procedure

Methyl 6-(4′-fluoro-[1,1′-biphenyl]-4-yl)-4-vinylpicolinate (600 mg, 1.8 mmol) was dissolved in 10 mL of methanol in a pressure tube. Into the tube was condensed about 10 mL ammonia at −20° C. to −30° C. The pressure tube was tightly closed and the resulting solution was stirred at room temperature for overnight. TLC (silica gel, 10% methanol in chloroform) showed the reaction had gone to completion. The ammonia was removed by nitrogen purge and the methanol was removed under reduced pressure to obtain 300 mg of 6-(4′-fluoro-[1,1′-biphenyl]-4-yl)-4-vinylpicolinamide which was pure enough to take to next step without purification.

Workup

  1. customThe pressure tube was tightly closed
  2. customThe ammonia was removed by nitrogen
  3. custompurge
  4. customthe methanol was removed under reduced pressure

Sources & evidence

ORD record
ord-329ca431f60540cd9843755cad9c7eb8
Source dataset
uspto-grants-2015_06
Patent number
US09056832B2

Reaction notes

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