Methylamine → HCID 13457769, compound

HRID 280139Notes

Reaction equation

HRID 280139 reaction equation
[F:1][C:2]1[CH:26]=[CH:25][CH:24]=[CH:23][C:3]=1[C:4]([C:6]1[N:7]([N:12]2C(=O)C3=CC=CC=C3C2=O)[C:8]([CH3:11])=[CH:9][CH:10]=1)=[O:5].CN>C(O)C.O>[NH2:12][N:7]1[C:8]([CH3:11])=[CH:9][CH:10]=[C:6]1[C:4](=[O:5])[C:3]1[CH:23]=[CH:24][CH:25]=[CH:26][C:2]=1[F:1]

Participants

5

Reactant 2

HCID 6329MethylamineHCID 23321783HCID 23321783, compound

Product 1

HCID 13457769HCID 13457769, compoundYield 83.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A rapidly stirred suspension of 2-(2-fluorobenzoyl)-5-methyl-1-phthalimidopyrrole (137 g, 0.39 mol) in 500 ml of 95% ethanol was treated with 230 ml of 40% w/w solution of methylamine and the mixture was further stirred at ambient temperature for 5 hours. The mixture was diluted with 300 ml of H2O and extracted with three 400 ml portions of dichloromethane. The combined extracts were dried (MgSO4), filtered, and evaporated to an oil which was purified by HPLC (silica gel, DCM) to give 71 g (83%) of an oil which solidified upon seeding. A three gram portion of this material was distilled at 120° (0.1 mmHg) to give 2.9 g of solid, m.p. 45°-48°.

Workup

  1. extractionextracted with three 400 ml portions of dichloromethane
  2. dry with materialThe combined extracts were dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated to an oil which
  5. customwas purified by HPLC (silica gel, DCM)

Sources & evidence

ORD record
ord-72f11836ba1c447391d7e958b338cd40
Source dataset
uspto-grants-1986_05
Patent number
US04588727

Reaction notes

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