Dichloromethane → HCID 178522848, compound

HRID 242125Notes

Reaction equation

HRID 242125 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][NH2:6].C([O:12][C:13]([C:15]1[C:16]([OH:30])=[N:17][C:18]2[C:23]([C:24]=1[OH:25])=[CH:22][CH:21]=[C:20]([C:26]([F:29])([F:28])[F:27])[CH:19]=2)=O)C.C(Cl)Cl>CCO>[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][NH:6][C:13]([C:15]1[C:16]([OH:30])=[N:17][C:18]2[C:23]([C:24]=1[OH:25])=[CH:22][CH:21]=[C:20]([C:26]([F:29])([F:27])[F:28])[CH:19]=2)=[O:12]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 668533-FluorobenzylamineHCID 178470057HCID 178470057, compound

Product 1

HCID 178522848HCID 178522848, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

2.0 ml (17.3 mmol) 3-fluorobenzylamine was added to a suspension of 1.3 g (4.3 mmol) 2,4-dihydroxy-7-(trifluoromethyl)quinoline-3-carboxylic acid ethyl ester in EtOH (50 ml) and the mixture was heated to 90° C. for 3 h. Concentration in a vacuum was subsequently carried out. After CC (DCM) of the residue, 1.6 g (4.2 mmol, 98%) N-(3-fluorobenzyl)-2,4-dihydroxy-7-(trifluoromethyl)quinoline-3-carboxylic acid amide was obtained.

Workup

  1. concentrationConcentration in a vacuum

Sources & evidence

ORD record
ord-ae858adc1ff54cc791714cfcf54246c0
Source dataset
uspto-grants-2014_02
Patent number
US08653101B2

Reaction notes

Loading…