HCID 178524010, compound → HCID 178477810, compound

HRID 1490310Notes

Reaction equation

HRID 1490310 reaction equation
[Br:1][C:2]1[CH:18]=[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)[C:3]=1[Cl:22]>C1(OC2C=CC=CC=2)C=CC=CC=1>[Br:1][C:2]1[CH:18]=[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)[C:3]=1[Cl:22]

Participants

3

Reactant 1

HCID 178524010HCID 178524010, compound

Product 1

HCID 178477810HCID 178477810, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 7583Diphenyl EtherSolvent

Procedure

7-Bromo-6-chloroquindoline-11-carboxylic acid from Example 77 (1.75 g, 4.66 mmol) was refluxed at 252° 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 to yield 1.48 g (96%) of the title compound as a brown solid; 1H NMR (DMSO-d6) δ 11.92 (s, 1H), 8.39 (s, 1H), 8.21 (d, J=8.4, 1H), 8.13 (d, J=7.6, 1H), 7.90 (d, J=8.4, 1H), 7.69 (t, J=7.6, 1H), 7.60 (td, J=7.6, J=1.6, 1H), 7.52 (d, J=8.8, 1H); 13C NMR (DMSO-d6) δ 143.88, 143.64, 143.59, 133.31, 132.56, 129.23, 127.82, 127.53, 126.62, 125.62, 119.09, 118.6, 113.96, 112.14, 111.89.

Workup

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

Sources & evidence

ORD record
ord-20f807663d234fd490d91653b16c5111
Source dataset
uspto-grants-1997_10
Patent number
US05681958

Reaction notes

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