p-Toluidine → HCID 178426356, compound

HRID 218094Notes

Reaction equation

HRID 218094 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([N:6]2[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:8](=O)[C:7]2=[O:16])=[CH:2]1.[NH2:17][C:18]1[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=1>CC(O)=O.CO>[CH3:24][C:21]1[CH:22]=[CH:23][C:18](/[N:17]=[C:8]2/[C:7](=[O:16])[N:6]([C:3]3[CH:4]=[CH:5][S:1][CH:2]=3)[C:14]3[C:9]/2=[CH:10][CH:11]=[CH:12][CH:13]=3)=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 7813p-ToluidineHCID 220224311-(3-Thienyl)-1H-indole-2,3-dione

Product 1

HCID 178426356HCID 178426356, compoundYield 50.5%

Reagents, catalysts & solvents 1

HCID 10129899Acetic acid methanolSolvent2×

Procedure

A solution of 1-(3-Thienyl)-1H-indole-2,3-dione (20 mg, 0.087 mmol) in 1% HOAc/MeOH (8 mL) was added to a solution of p-toluidine (19 mg, 0.18 mmol) in 1% HOAc/MeOH (8 mL). The reaction mixture was stirred for 12 h at room temperature, heated at 50° C. for 1 h, and concentrated in vacuo. The residue was purified by preparative TLC on silica using EtOAc/hexanes (3:7, 0.1% TEA) giving the desired product (14 mg, 50%).

Workup

  1. temperatureheated at 50° C. for 1 h
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by preparative TLC on silica

Sources & evidence

ORD record
ord-728398b9f7f147ea91e87359ca219f29
Source dataset
uspto-grants-2012_06
Patent number
US08198313B2

Reaction notes

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