Acetic Acid → HCID 22668268, compound

HRID 456920Notes

Reaction equation

HRID 456920 reaction equation
C([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([C:13](OC(C)(C)C)=[O:14])[C:8]([C:20]1C(Cl)=[N:22][C:23]3[C:28]([CH:29]=1)=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:7]2)(=O)C.[C:31](O)(=[O:33])[CH3:32]>O>[C:31]([C:26]1[CH:27]=[C:28]2[C:23](=[CH:24][CH:25]=1)[NH:22][C:20]([C:8]1[C:13](=[O:14])[NH:9][C:10]3[C:6]([CH:7]=1)=[CH:5][CH:4]=[CH:12][CH:11]=3)=[CH:29]2)(=[O:33])[CH3:32]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 22668263HCID 22668263, compound

Product 1

HCID 22668268HCID 22668268, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of tert-butyl 5-acetyl-2-(2-chloro-3-quinolinyl)-1H-indole-1-carboxylate (8-3, 400 mg, 0.95 mmol) was heated in a 3:1 mixture of acetic acid and water at reflux for 20 hours. The reaction mixture was cooled, then concentrated to dryness. The residue was suspended in ethyl ether (50 mL) with the aid of sonication, then filtered and air dried to give 3-(5-acetyl-1H-indol-2-yl)-2(1H)-quinolinone (8-4) as a yellow solid. 1H NMR (400 MHz, DMSO) δ 12.22 (s, 1H), 11.94 (s, 1H), 8.59 (s, 1H), 8.31 (s, 1H), 7.76 (d, 2H, J=7.9 Hz), 7.60 (d, 1H, J=8.6 Hz), 7.55 (t, 1H, J=7.5 Hz), 7.49 (s, 1H), 7.39 (d, 1H, J=7.9 Hz), 7.26 (t, 1H, J=7.5 Hz), 2.62 (s, 3H).

Workup

  1. temperatureat reflux for 20 hours
  2. temperatureThe reaction mixture was cooled
  3. concentrationconcentrated to dryness
  4. customThe residue was suspended in ethyl ether (50 mL) with the aid of sonication
  5. filtrationfiltered
  6. customair dried

Sources & evidence

ORD record
ord-3137d9b40b244e2ea7602e927c0ab760
Source dataset
uspto-grants-2007_03
Patent number
US07186723B2

Reaction notes

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