Hydrochloric Acid → HCID 86736998, compound

HRID 1395647Notes

Reaction equation

HRID 1395647 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5](Cl)=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[CH3:12][C:13]1[C:19]([C:20]([F:23])([F:22])[F:21])=[CH:18][CH:17]=[CH:16][C:14]=1[NH2:15].C1(O)C=CC=CC=1.C(=O)(O)[O-].[Na+].Cl>[OH-].[Na+].CCOCC>[Br:1][C:2]1[CH:3]=[N:4][C:5]([NH:15][C:14]2[CH:16]=[CH:17][CH:18]=[C:19]([C:20]([F:21])([F:22])[F:23])[C:13]=2[CH3:12])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 996PhenolHCID 516892Sodium BicarbonateHCID 2735932Trifluoromethyl toluidineHCID 27633425-Bromo-2-chloronicotinic acid

Product 1

HCID 86736998HCID 86736998, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
170 °C

Procedure

Heat in an oil bath at 170° C. a mixture of 15 g. of 5-bromo-2-chloro-nicotinic acid, 12.2 g. of 2-methyl-3-trifluoromethyl aniline and 60 g. of phenol for three hours. Treat the resulting reaction mixture with ether and 5% sodium bicarbonate solution, concentrate and steam distil to obtain an oily residue. Dissolve the oily residue in dilute sodium hydroxide solution, acidify with dilute hydrochloric acid and filter. Recrystallize the product from methanol to yield 5-bromo-2-(2-methyl-3-trifluoromethylanilino) nicotinic acid, m.p. 222°-224° C.

Workup

  1. additiona mixture of 15 g
  2. additionTreat
  3. concentrationconcentrate
  4. customsteam distil
  5. customto obtain an oily residue
  6. filtrationfilter
  7. customRecrystallize the product from methanol

Sources & evidence

ORD record
ord-be8b32be4f2945e0b4fd23be241c7ed7
Source dataset
uspto-grants-1980_05
Patent number
US04205073

Reaction notes

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