HCID 178524014, compound → HCID 178477821, compound

HRID 1490308Notes

Reaction equation

HRID 1490308 reaction equation
[Br:1][C:2]1[C:18]([Cl:19])=[CH:17][C:16]2[C:4](=[C:5]3[C:14]([N:15]=2)=[C:13](C(O)=O)[C:12]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[NH:6]3)[CH:3]=1>C1(OC2C=CC=CC=2)C=CC=CC=1>[Br:1][C:2]1[C:18]([Cl:19])=[CH:17][C:16]2[C:4](=[C:5]3[C:14]([N:15]=2)=[CH:13][C:12]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[NH:6]3)[CH:3]=1

Participants

3

Reactant 1

HCID 178524014HCID 178524014, compound

Product 1

HCID 178477821HCID 178477821, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 7583Diphenyl EtherSolvent

Procedure

7-Bromo-8-chloroquindoline-11-carboxylic acid from Example 74 (3.00 g, 7.99 mmol) was refluxed at 250° C. in diphenyl ether (30 mL) for 4 hours in an oversize flask. The mixture was cooled, diluted with petroleum ether (30 mL), and filtered. The filter cake was washed with petroleum ether (100 mL) and dried under high vacuum to yield 2.49 g (94%) of the title compound as a greenish solid, mp >246° C.; 1H NMR (DMSO-d6) δ 11.70 (s, 1H), 8.62 (s, 1H), 8.36 (s, 1H), 8.18 (d, J=8.4, 1H), 8.12 (d, J=8.4, 1H), 7.84 (s, 1H),7.69 (t, J=6.8, 1H), 7.59 (t, J=7.2, 1H); 13C NMR (DMSO-d6) δ 143.65, 143.15, 133.39, 132.95, 128.65, 127.66, 127.97, 126.75, 125.51 (two signals), 121.53, 114.34, 113.10, 111.11; MS (EI, m/z) 331.9 (M+2+).

Workup

  1. temperatureThe mixture was cooled
  2. filtrationfiltered
  3. washThe filter cake was washed with petroleum ether (100 mL)
  4. customdried under high vacuum

Sources & evidence

ORD record
ord-55edbdc8400e45fcb023265993613e1f
Source dataset
uspto-grants-1997_10
Patent number
US05681958

Reaction notes

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