Acetic Acid → HCID 22668268, compound

HRID 1007658Notes

Reaction equation

HRID 1007658 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 h 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 h The reaction mixture
  2. temperaturewas 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-948a9aac3dd2400a9c6a5a50123ee474
Source dataset
uspto-grants-2004_09
Patent number
US06794393B1

Reaction notes

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