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

HRID 280115Notes

Reaction equation

HRID 280115 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 L g oil, half of which was purified by Kugelrohr distillation (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 L g oil, half of which
  7. distillationwas purified by Kugelrohr distillation (120°-130° at 0.2 mm Hg)

Sources & evidence

ORD record
ord-dc1a0d691de7435da2494afb2f5a93d6
Source dataset
uspto-grants-1986_05
Patent number
US04588727

Reaction notes

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