Methylamine → 1-Amino-2-(2-fluorobenzoyl)pyrrole

HRID 462739Notes

Reaction equation

HRID 462739 reaction equation
[F:1][C:2]1[CH:25]=[CH:24][CH:23]=[CH:22][C:3]=1[C:4]([C:6]1[N:7]([N:11]2C(=O)C3=CC=CC=C3C2=O)[CH:8]=[CH:9][CH:10]=1)=[O:5].CN>CN(C=O)C.O>[NH2:11][N:7]1[CH:8]=[CH:9][CH:10]=[C:6]1[C:4](=[O:5])[C:3]1[CH:22]=[CH:23][CH:24]=[CH:25][C:2]=1[F:1]

Participants

5

Reactant 2

HCID 6329MethylamineHCID 134577152-(2-Fluorobenzoyl)-1-phthalimidopyrrole

Product 1

HCID 134577161-Amino-2-(2-fluorobenzoyl)pyrroleYield 93%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a suspension of 2-(2-fluorobenzoyl)-1-phthalimidopyrrole (12.5 g, 27 mmole) in 40 ml DMF was added 40 ml methylamine (40% solution in water). After stirring one hour at ambient temperature, the reaction mixture was diluted with water and extracted with ether. The organic extract was washed with water and with saturated NaCl solution, dried over anhydrous MgSO4, filtered and evaporated to 9 g oil, half of which was purified by Kugelrohr distallation (120°-130° at 0.2 mm Hg) to give 3.5 g (93%) solid, m.p. 44°-47°.

Workup

  1. extractionextracted with ether
  2. extractionThe organic extract
  3. washwas washed with water and with saturated NaCl solution
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. customevaporated to 9 g oil, half of which
  7. customwas purified by Kugelrohr distallation (120°-130° at 0.2 mm Hg)

Sources & evidence

ORD record
ord-064dc037ee864b59b224eb94988adb36
Source dataset
uspto-grants-1985_05
Patent number
US04517195

Reaction notes

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