Methylamine → HCID 13457740, compound

HRID 280121Notes

Reaction equation

HRID 280121 reaction equation
[Cl: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>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[Cl:1]

Participants

5

Reactant 2

HCID 6329MethylamineHCID 13457735HCID 13457735, compound

Product 1

HCID 13457740HCID 13457740, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

2-(2-chlorobenzoyl)-1-phthalimidopyrrole (40 g, 0.114 mol) was suspended in 350 ml of 95% ethanol. To this rapidly stirred slurry was added 50 ml of a 40% aqueous solution of methylamine over 10 minutes. After 2.5 hours of rapid stirring the mixture was diluted with 400 ml of water and extracted with four 200 ml portions of ether. The combined extracts were washed with water, dried over anhydrous MgSO4, filtered and evaporated to an oil which solidified upon standing. Trituration of this solid with hexane and collection upon a filter yielded 23.6 g (94%) of solid, m.p. 76°-78°.

Workup

  1. extractionextracted with four 200 ml portions of ether
  2. washThe combined extracts were washed with water
  3. dry with materialdried over anhydrous MgSO4
  4. filtrationfiltered
  5. customevaporated to an oil which
  6. customTrituration of this solid with hexane and collection upon a filter

Sources & evidence

ORD record
ord-8e022944b64b4969b119949d3c48572c
Source dataset
uspto-grants-1986_05
Patent number
US04588727

Reaction notes

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