Aniline → HCID 9882454, compound

HRID 1451286Notes

Reaction equation

HRID 1451286 reaction equation
[C:1]1(=[O:16])[C:13]2[C:12]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[NH:6][C:5](=[O:14])[C:4]=2[C:3](=[O:15])O1.[NH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(N1C=CN=C1)(N1C=CN=C1)=O>CN(C)C=O>[C:18]1([N:17]2[C:1](=[O:16])[C:13]3[C:12]4[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=4[NH:6][C:5](=[O:14])[C:4]=3[C:3]2=[O:15])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 6115AnilineHCID 682631,1'-CarbonyldiimidazoleHCID 15228889HCID 15228889, compound

Product 1

HCID 9882454HCID 9882454, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of Furo[3,4-c]quinoline-1,3,4(5H)-trione (215 mg) and aniline (93 mg) in dry dimethylformamide (3 mL) was heated at 100° C. for 5 min. After coolong to room temperature 1,1'-Carbonyldiimidazole (200 mg) was added. The reaction mixture was then heated again to 100° C. for an additional 5 min. After cooling the reaction mixture was poured onto water to afford 2-Phenyl-pyrrolo[3,4-c]quinoline-1,3,4(5H)-trione (Compound 1) as yellow crystals melting at >390° C.

Workup

  1. customAfter coolong to room temperature
  2. additionwas added
  3. temperatureThe reaction mixture was then heated again to 100° C. for an additional 5 min
  4. temperatureAfter cooling the reaction mixture
  5. additionwas poured onto water

Sources & evidence

ORD record
ord-368158d03b3647d99265c34de6d8fc9d
Source dataset
uspto-grants-1997_02
Patent number
US05604235

Reaction notes

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