HCID 178524013, compound → HCID 178505462, compound

HRID 1490307Notes

Reaction equation

HRID 1490307 reaction equation
[F:1][C:2]1[CH:18]=[CH:17][C:16]2[NH:15][C:14]3[C:6]([N:7]=[C:8]4[C:13]=3[CH:12]=[CH:11][CH:10]=[CH:9]4)=[C:5](C(O)=O)[C:4]=2[CH:3]=1>C1(OC2C=CC=CC=2)C=CC=CC=1>[F:1][C:2]1[CH:18]=[CH:17][C:16]2[NH:15][C:14]3[C:6]([N:7]=[C:8]4[C:13]=3[CH:12]=[CH:11][CH:10]=[CH:9]4)=[CH:5][C:4]=2[CH:3]=1

Participants

3

Reactant 1

HCID 178524013HCID 178524013, compound

Product 1

HCID 178505462HCID 178505462, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 7583Diphenyl EtherSolvent

Procedure

2-Fluoroquindoline-11-carboxylic acid from Example 71 (4.50 g, 16.1 mmol) was refluxed at 250° C. in diphenyl ether (40 mL) for 4 hours. The mixture was cooled, diluted with petroleum ether (40 mL), and filtered. The filter cake was washed with petroleum ether (100 mL) and dried. The crude material was added to methanol (250 mL) and filtered, washing with additional methanol (2×75 mL). Concentration of the filtrate afforded 2.47 g (65%) of the title compound as a brown solid, mp >246° C.; 1H NMR (DMSO-d6) δ 11.52 (s, 1H), 8.34 (d, J=8, 1H), 8.28 (s, 1H), 8.24 (dd, J=9.2, J=5.6, 1H), 7.90 (dd, J=10, J=2.8, 1H), 7.50-7.65 (m, 3H), 7.29 (t, J=8, 1H); 13C NMR (DMSO-d6) δ 158.96 (J=244), 145.53, 143.97, 140.42, 132.86, 131.22 (J=10), 129.83, 127.25, 121.31, 120.84, 119.54, 116.23 (J=27), 112.47 (J=5.3), 111.58, 110.01 (J=22); MS (EI, m/z) 236.1 (M+).

Workup

  1. temperatureThe mixture was cooled
  2. filtrationfiltered
  3. washThe filter cake was washed with petroleum ether (100 mL)
  4. customdried
  5. additionThe crude material was added to methanol (250 mL)
  6. filtrationfiltered
  7. washwashing with additional methanol (2×75 mL)

Sources & evidence

ORD record
ord-bbf1650030c24b90b348539c06b01cbe
Source dataset
uspto-grants-1997_10
Patent number
US05681958

Reaction notes

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