Benzene → HCID 19392557, compound

HRID 1193756Notes

Reaction equation

HRID 1193756 reaction equation
C([N:4]1[CH:8]=[CH:7][C:6](N2CCCC2)=[C:5]1[C:14]([C:16]1[C:17]([NH:22][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[CH:24]=2)=[N:18][CH:19]=[CH:20][CH:21]=1)=[O:15])(=O)C.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C1C=CC=CC=1>C(O)(C)(C)C>[Cl:29][C:25]1[CH:24]=[C:23]([N:22]2[C:17]3[N:18]=[CH:19][CH:20]=[CH:21][C:16]=3[C:14](=[O:15])[C:5]3[NH:4][CH:8]=[CH:7][C:6]2=3)[CH:28]=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 241BenzeneHCID 521998p-Toluenesulfonic acid monohydrateHCID 14423304HCID 14423304, compound

Product 1

HCID 19392557HCID 19392557, compound

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

Reflux a mixture of 1-acetyl-2-[2-[(3-chlorophenyl)amino]-3-pyridinylcarbonyl]-3-(1-pyrrolidinyl)-1H-pyrrole (0.45 g), p-toluenesulfonic acid monohydrate (0.21 g) in a solvent of benzene (20 ml), and tert-butanol for 12 hours. Evaporate solvent and partition the residue between CHCl3 and 1M NaHCO3. Wash the CHCl3 solution with water, dry and filter the solution. Evaporate the solvent, and triturate the residue with CHCl3 to give 4-(3-chlorophenyl)-1,4-dihydro-9H-pyrrolo[3,2-b][1,8]naphthyridin-9-one, m.p. 300°-301° C.

Workup

  1. temperatureReflux
  2. customEvaporate solvent and partition the residue between CHCl3 and 1M NaHCO3
  3. washWash the CHCl3 solution with water
  4. customdry
  5. filtrationfilter the solution
  6. customEvaporate the solvent
  7. customtriturate the residue with CHCl3

Sources & evidence

ORD record
ord-36c52d9d75634f3e8330140502f395b0
Source dataset
uspto-grants-1989_03
Patent number
US04810708

Reaction notes

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