Aniline → HCID 18667506, compound

HRID 1060024Notes

Reaction equation

HRID 1060024 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([O:14][CH3:15])[CH:11]=[CH:10][N:9]=2)=[CH:4][C:3]=1[N+:16]([O-:18])=[O:17].C(N(CC)CC)C.[NH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>O1CCCC1>[CH3:15][O:14][C:12]1[CH:11]=[CH:10][N:9]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([NH:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[C:3]([N+:16]([O-:18])=[O:17])[CH:4]=2)[CH:13]=1

Participants

5

Reactant 3

HCID 6115AnilineHCID 8471TriethylamineHCID 18667517HCID 18667517, compound

Product 1

HCID 18667506HCID 18667506, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-fluoro-4-(4-methoxypyridin-2-yl)-2-nitrobenzene (200 mg) and triethylamine (0.135 ml) in tetrahydrofuran (2 ml) was added aniline (2 ml). The mixture was stirred under reflux for 6 hours and evaporated under reduced pressure. The residue was dissolved in ethyl acetate and washed with water and brine, dried over magnesium sulfate and evaporated under reduced pressure. The precipitate was triturated with diisopropyl ether, collected by filtration and dried to give 4-(4-methoxypyridin-2-yl)-2-nitro-N-phenylaniline (235 mg).

Workup

  1. temperatureunder reflux for 6 hours
  2. customevaporated under reduced pressure
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated under reduced pressure
  7. customThe precipitate was triturated with diisopropyl ether
  8. filtrationcollected by filtration
  9. customdried

Sources & evidence

ORD record
ord-de7d45c46a214c3292da1684e2d78d9d
Source dataset
uspto-grants-2003_02
Patent number
US06521643B1

Reaction notes

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