1,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene) → 7-Iodo-6-methylquinolin-4(1H)-one

HRID 1829765Notes

Reaction equation

HRID 1829765 reaction equation
[I:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:15])[C:7](C(O)=O)=[CH:8][NH:9]2)=[CH:4][C:3]=1[CH3:16].C1C=CC(C2C=CC=CC=2)=CC=1.C1C=CC(OC2C=CC=CC=2)=CC=1>CCCCCCC>[I:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:15])[CH:7]=[CH:8][NH:9]2)=[CH:4][C:3]=1[CH3:16]

Participants

4

Reactant 2

HCID 246701,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene)HCID 220544887-Iodo-6-methyl-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid

Product 1

HCID 220545057-Iodo-6-methylquinolin-4(1H)-oneYield 91%

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Procedure

Under vigorous stirring, 7-iodo-6-methyl-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid (6.50 g, 19.8 mmol) was added portionwise to Dowtherm® A (120 mL) at 250° C., then the mixture was stirred for another 90 min. After cooling, heptane (170 mL) was added, and the precipitate was collected by filtration. The crude material was triturated in hexane/ethyl acetate (1:1) to afford the title compound (5.12 g, 91%). Off-white solid, ISP-MS: m/e=286.1 ([M+H]+).

Workup

  1. temperatureAfter cooling
  2. filtrationthe precipitate was collected by filtration
  3. customThe crude material was triturated in hexane/ethyl acetate (1:1)

Sources & evidence

ORD record
ord-7b7c2351ad6f4ecdb6cfaf3c98b52d6c
Source dataset
uspto-grants-2006_06
Patent number
US07064134B2

Reaction notes

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