Ethanol → HCID 135834141, compound

HRID 1017724Notes

Reaction equation

HRID 1017724 reaction equation
[CH:1]([C:3]1[C:8](OC)=[CH:7][CH:6]=[CH:5][C:4]=1[NH:11][C:12](=[O:18])OC(C)(C)C)=O.[NH:19]1[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=2[N:21]=[C:20]1[CH2:28]C(OCC)=O.N1CCCCC1.[CH2:40]([OH:42])C>>[NH:19]1[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=2[N:21]=[C:20]1[C:28]1[C:12](=[O:18])[NH:11][C:4]2[C:3]([CH:1]=1)=[CH:8][CH:7]=[CH:6][C:5]=2[O:42][CH3:40]

Participants

5

Reactant 4

HCID 702EthanolHCID 8082PiperidineHCID 308071ethyl 2-(1H-1,3-benzodiazol-2-yl)acetateHCID 22897235HCID 22897235, compound

Product 1

HCID 135834141HCID 135834141, compound

Procedure

A solution of tert-butyl 2-formyl-3-methoxyphenylcarbamate (13-1, 0.50 g, 1.9 mmol, 1 equiv, prepared by the formylation method utilized in the examples above), ethyl 1H-benzimidazol-2-ylacetate (0.39 g, 1.9 mmol, 1.0 equiv, prepared by the method of Rahmouni, M, Derdour, A., Bazureau, J., and Hamelin Tetrahedron Lett. 1994, 35, 4563-4564), and piperidine (0.090 mL, 0.91 mmol, 0.48 equiv) in ethanol (50 mL) was heated at reflux for 20 h. The reaction mixture was cooled and the precipitate which formed was filtered and air dried to give 3-(1H-benzimidazol-2-yl)-8-methoxy-2(1H)-quinolinone (13-2). 1H NMR (400 MHz, DMSO-d6) δ 12.59 (s, 1H), 12.43 (s, 1H), 9.25 (s, 1H), 7.71 (m, 1H), 7.66 (m, 1H), 7.55 (t, 1H, J=8.2 Hz), 7.20 (m, 2H), 7.03 (d, 1H, J=8.2 Hz), 6.85 (d, 1H, J=8.2 Hz).

Workup

  1. customprepared by the method of Rahmouni, M, Derdour
  2. temperatureat reflux for 20 h
  3. temperatureThe reaction mixture was cooled
  4. customthe precipitate which formed
  5. filtrationwas filtered
  6. customair dried

Sources & evidence

ORD record
ord-9fc2e3f719dd4c25a1bd6ccf7b67a8fc
Source dataset
uspto-grants-2002_11
Patent number
US06479512B1

Reaction notes

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