Indole → N-[2-(1H-indol-2-yl)-phenyl]phthalamic acid

HRID 1272460Notes

Reaction equation

HRID 1272460 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[NH:9][C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[CH:12][CH:11]=2.N1C2C(=CC=CC=2)C=C1.[C:26]1(=[O:36])[O:31][C:29](=[O:30])[C:28]2=[CH:32][CH:33]=[CH:34][CH:35]=[C:27]12>ClCCl.CN(C1C=CN=CC=1)C>[NH:9]1[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:16]=[C:8]1[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[NH:1][C:26](=[O:36])[C:27]1[C:28](=[CH:32][CH:33]=[CH:34][CH:35]=1)[C:29]([OH:31])=[O:30]

Participants

6

Reactant 3

HCID 798IndoleHCID 6811Phthalic AnhydrideHCID 7359662-(2-Aminophenyl)indole2×

Product 1

HCID 10316222N-[2-(1H-indol-2-yl)-phenyl]phthalamic acidYield 104.7%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A 100-mL, one-necked, round bottomed flask with a magnetic stirring bar and a septum was charged with 2-(2-aminophenyl) indole (210 mg; 1.01 mmol). The indole was dissolved in ca. 7 mL of dichloromethane to give a very pale yellow solution. DMAP (143 mg; 1.17 mmol; 1.16 equiv) and phthalic anhydride (179 mg; 1.21 mmol; 1.20 equiv) were added sequentially each dissolving completely with a resulting yellow solution. The solution was stirred at room temperature, and the reaction was followed by TLC, and showed complete conversion in ca. 30 min as indicated by the disappearance of the 2-(2-aminophenyl) indole. The reaction mixture was poured into a 125-mL separatory funnel and extracted with 15 mL HCl (aq, ca. 1 M). The aqueous layer was washed with 2×5 mL CH2Cl2, and the combined organic layer was dried (anhydrous Na2SO4), filtered, and concentrated by rotary evaporation to yield a canary yellow foamy solid (0.377 g) of N-[2-(1H-indol-2-yl)-phenyl]phthalamic acid. MS (M+H+: calcd 357; found 357).

Workup

  1. customto give a very pale yellow solution
  2. customin ca. 30 min
  3. additionThe reaction mixture was poured into a 125-mL separatory funnel
  4. extractionextracted with 15 mL HCl (aq, ca. 1 M)
  5. washThe aqueous layer was washed with 2×5 mL CH2Cl2
  6. dry with materialthe combined organic layer was dried (anhydrous Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-4e555e679fee4c1f885db7cebce69638
Source dataset
uspto-grants-2007_04
Patent number
US07208493B2

Reaction notes

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