2,4-Difluoroaniline → HCID 58962861, compound

HRID 917739Notes

Reaction equation

HRID 917739 reaction equation
[F:1][C:2]1[CH:8]=[C:7]([F:9])[CH:6]=[CH:5][C:3]=1[NH2:4].Cl[C:11]1[C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:15][N:14]=[C:13]([Cl:22])[CH:12]=1>CCO.Cl.O>[Cl:22][C:13]1[CH:12]=[C:11]([NH:4][C:3]2[CH:5]=[CH:6][C:7]([F:9])=[CH:8][C:2]=2[F:1])[C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:15][N:14]=1

Participants

6

Reactant 2

HCID 97092,4-DifluoroanilineHCID 600045Ethyl 4,6-dichloropyridine-3-carboxylate

Product 1

HCID 58962861HCID 58962861, compoundYield 64.3%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 962WaterCatalystHCID 702EthanolSolvent

Procedure

2,4-Difluoroaniline (1.20 g, 9.3 mmol) and ethyl 4,6-dichloronicotinate (2.05 g, 9.3 mmol) were dissolved in a mixture of EtOH (40 ml) and conc. HCl (5 drops) and heated to reflux for 15 h. The solution was allowed to cool and H2O (3 drops) was added to initialize precipitation. The flask was then sealed and placed in a freezer for 3 h. The solid was then isolated by filtration and washed with 10% Et2O/Hexane, affording ethyl 6-chloro-4-(2,4-difluoroanilino)nicotinate (1.87 g, 64%); m.p. (EtOH/water) 107-109° C. 1H NMR [400 MHz, CDCl3] δ 9.62 (br s, 1H), 8.79 (s, 1H), 7.35-7.29 (m, 1H), 7.02-6.95 (m, 2H), 6.58 (d, J=1.5 Hz, 1H), 4.42 (q, J=7.1 Hz, 2H), 1.43 (t, J=7.1 Hz, 3H). MS (FAB+) 313 (50%).

Workup

  1. temperatureheated
  2. temperatureto reflux for 15 h
  3. temperatureto cool
  4. customprecipitation
  5. customThe flask was then sealed
  6. customThe solid was then isolated by filtration
  7. washwashed with 10% Et2O/Hexane

Sources & evidence

ORD record
ord-f727813195964bfeac79999c67e2485e
Source dataset
uspto-grants-2007_09
Patent number
US07273877B2

Reaction notes

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