HCID 178524012, compound → HCID 178420006, compound

HRID 1490264Notes

Reaction equation

HRID 1490264 reaction equation
[CH:1]1[C:17]2[C:16](C(O)=O)=[C:15]3[C:7](=[C:8]4[C:13](=[N:14]3)[CH:12]=[CH:11][CH:10]=[CH:9]4)[NH:6][C:5]=2[CH:4]=[CH:3][CH:2]=1>C1(OC2C=CC=CC=2)C=CC=CC=1>[CH:1]1[C:17]2[CH:16]=[C:15]3[C:7](=[C:8]4[C:13](=[N:14]3)[CH:12]=[CH:11][CH:10]=[CH:9]4)[NH:6][C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 1

HCID 178524012HCID 178524012, compound

Product 1

HCID 178420006HCID 178420006, compoundYield 91.2%

Reagents, catalysts & solvents 1

HCID 7583Diphenyl EtherSolvent

Conditions

Temperature
30 °C

Procedure

A mixture of quindoline-11-carboxylic acid prepared in Example 1 (29.2 g, 0.111 mol) and diphenylether (300 mL) was refluxed for 6 hours, cooled to 30° C. and diluted with petroleum ether (250 mL). The precipitate which formed was filtered and washed with petroleum ether thoroughly, yielding 22.1 g (90.9%) of the title compound. A portion of this material was further purified by LPLC (ethyl acetate-hexane 1:3), mp 249°-251° C. [lit 251°-252° C. (Degutis, Y. A.; Ezyarskaite, A. B. Khim. Geterotsik. Soedin. 1986, 1375)]; 1H NMR (DMSO-d6) δ 11.43 (s, 1H, NH), 8.36 (d, J=7.8, 1H), 8.29 (s, 1H), 8.19 (d, J=8.4, 1H), 8.10 (d, J=8.2, 1H), 7.67-7.53 (m, 4H), 7.27 (t, J=7.4, 1H); 13C NMR (DMSO-d6) δ 145.72, 144.03, 143.39, 132.44, 129.68, 128.68, 127.48, 126.71, 126.01, 124.84, 121.34, 120.97, 119.33, 112.99, 111.49; MS (EI, m/z) 218.1 (M+).

Workup

  1. temperaturewas refluxed for 6 hours
  2. customThe precipitate which formed
  3. filtrationwas filtered
  4. washwashed with petroleum ether thoroughly

Sources & evidence

ORD record
ord-5b3a497a146948fb978f70677e861f94
Source dataset
uspto-grants-1997_10
Patent number
US05681958

Reaction notes

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