1,2-Dichloroethane → 3,4,5-trihydroxy-N-[2-(1H-indol-2-yl)-phenyl]-benzamide

HRID 1272459Notes

Reaction equation

HRID 1272459 reaction equation
[C:1]([OH:12])(=O)[C:2]1[CH:10]=[C:8]([OH:9])[C:6]([OH:7])=[C:4]([OH:5])[CH:3]=1.C(Cl)CCl.[NH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[C:24]1[NH:25][C:26]2[C:31]([CH:32]=1)=[CH:30][CH:29]=[CH:28][CH:27]=2>ClCCl>[OH:9][C:8]1[CH:10]=[C:2]([CH:3]=[C:4]([OH:5])[C:6]=1[OH:7])[C:1]([NH:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[C:24]1[NH:25][C:26]2[C:31]([CH:32]=1)=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:12]

Participants

5

Reactant 3

HCID 111,2-DichloroethaneHCID 370Gallic AcidHCID 7359662-(2-Aminophenyl)indole

Product 1

HCID 100214123,4,5-trihydroxy-N-[2-(1H-indol-2-yl)-phenyl]-benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 25-mL one-necked recovery flask equipped with a stirring bar and a septum was charged with gallic acid (176 mg; 1.03 mmol; 1.00 equiv). A clear, colorless solution was formed on addition of 5 mL of dichloromethane. Solid EDC (197 mg; 1.03 mmol; 1.00 equiv) and 2-(2-aminophenyl)indole (194 mg; 0.932 mmol; 0.904 equiv) were added sequentially as solids. The reaction was worked up after 24 h by extraction with 10 mL of NaHCO3 (satd aq). The organic layer was dried (anhydrous sodium sulfate), filtered and concentrated by rotary evaporation to yield a yellow oily paste. The crude was purified using DCM-MeOH (19:1) to yield a light yellow solid (230 mg; 68%).

Workup

  1. customA 25-mL one-necked recovery flask equipped with a stirring bar
  2. extractionThe reaction was worked up after 24 h by extraction with 10 mL of NaHCO3 (satd aq)
  3. dry with materialThe organic layer was dried (anhydrous sodium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated by rotary evaporation
  6. customto yield a yellow oily paste
  7. customThe crude was purified
  8. customto yield a light yellow solid (230 mg; 68%)

Sources & evidence

ORD record
ord-b0e2da68436c498d881fd055421c1395
Source dataset
uspto-grants-2007_04
Patent number
US07208493B2

Reaction notes

Loading…