Methylamine → HCID 13457732, compound

HRID 280116Notes

Reaction equation

HRID 280116 reaction equation
[C:1]([C:9]1[N:10]([N:14]2C(=O)C3=CC=CC=C3C2=O)[CH:11]=[CH:12][CH:13]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN>C(O)C.O>[NH2:14][N:10]1[CH:11]=[CH:12][CH:13]=[C:9]1[C:1](=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 6329MethylamineHCID 13457731HCID 13457731, compound

Product 1

HCID 13457732HCID 13457732, compoundYield 102.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a suspension of 2-benzoyl-1-phthalimidopyrrole (35 g, 0.11 mole) in 350 ml ethanol was slowly added 45 ml methylamine (40% solution in water). After stirring two hours at ambient temperature, the mixture was diluted with 40 ml water and extracted with ether. The ether extract was washed with water and saturated NaCl solution, dried over anhydrous MgSO4, filtered and evaporated to 28 g oil which upon trituration with hexanes gave 21 g (99%) solid, m.p. 65°-69°. 3.5 g of this material was purified by HPLC (silica gel, 4% ethyl acetate/dichloromethane) to give 2.8 g solid, which was recrystallized from hexanes to give 2.4 g solid, m.p. 65°-67°.

Workup

  1. extractionextracted with ether
  2. extractionThe ether extract
  3. washwas washed with water and saturated NaCl solution
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. customevaporated to 28 g oil which upon trituration with hexanes

Sources & evidence

ORD record
ord-fa4eb6bea9df4c998342f7be30a95997
Source dataset
uspto-grants-1986_05
Patent number
US04588727

Reaction notes

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