Phosgene → pyrrolo[1,2-a]quinoxalin-4(5H)-one

HRID 1449485Notes

Reaction equation

HRID 1449485 reaction equation
[N:1]1([C:6]2[CH:12]=[CH:11][CH:10]=[CH:9][C:7]=2[NH2:8])[CH:5]=[CH:4][CH:3]=[CH:2]1.[C:13](Cl)(Cl)=[O:14]>C1(C)C=CC=CC=1>[O:14]=[C:13]1[NH:8][C:7]2[C:6](=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:1]2[CH:2]=[CH:3][CH:4]=[C:5]12

Participants

4

Reactant 2

HCID 6371PhosgeneHCID 801232-(1H-pyrrol-1-yl)aniline

Product 1

HCID 2740936pyrrolo[1,2-a]quinoxalin-4(5H)-one

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

15 g (0.095 mol) of 2-(1-pyrrolyl)aniline is brought to reflux for 1 h 30 min, in 200 cm3 of toluene, in the presence of 50 cm3 of a 20% solution of phosgene in toluene. After cooling, the precipitate formed is filtered off, washed with ethyl ether, dried and recrystallized from acetonitrile (white powder sublimed at 270° C.).

Workup

  1. temperatureAfter cooling
  2. customthe precipitate formed
  3. filtrationis filtered off
  4. washwashed with ethyl ether
  5. customdried
  6. customrecrystallized from acetonitrile (white powder sublimed at 270° C.)

Sources & evidence

ORD record
ord-258dd5dc38914bef95f011ce80bb98eb
Source dataset
uspto-grants-1997_02
Patent number
US05599812

Reaction notes

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