Diethyl Ether → 2-[(3-Trifluoromethylphenyl)amino]-3-pyridylmethanol

HRID 2372753Notes

Reaction equation

HRID 2372753 reaction equation
C(OCC)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH:12]1[CH:13]=[C:14]([C:28]([F:31])([F:30])[F:29])[CH:15]=[C:16]([NH:18][C:19]2[N:24]=[CH:23][CH:22]=[CH:21][C:20]=2[C:25](O)=[O:26])[CH:17]=1.S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1.C(OCC)(=O)C>[F:30][C:28]([F:29])([F:31])[C:14]1[CH:15]=[C:16]([NH:18][C:19]2[C:20]([CH2:25][OH:26])=[CH:21][CH:22]=[CH:23][N:24]=2)[CH:17]=[CH:12][CH:13]=1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 4488Niflumic AcidHCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydride

Product 1

HCID 135776882-[(3-Trifluoromethylphenyl)amino]-3-pyridylmethanolYield 85%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

500 ml of anhydrous ethyl ether are run gently onto 26 g of lithium aluminum hydride, and 100 g of niflumic acid, dissolved in 250 ml of anhydrous tetrahydrofuran, are then added dropwise. The mixture is then brought to reflux for 3 hours. After cooling, it is hydrolyzed with 150 ml of ethyl acetate and 100 ml of saturated sodium sulfate solution. After filtration, the filtrate is concentrated to obtain the expected compound in the form of a yellow solid.

Workup

  1. additionare then added dropwise
  2. temperatureto reflux for 3 hours
  3. temperatureAfter cooling
  4. filtrationAfter filtration
  5. concentrationthe filtrate is concentrated

Sources & evidence

ORD record
ord-c48aa1175c95456d94d2b70ee0400e9d
Source dataset
uspto-grants-1992_03
Patent number
US05100902

Reaction notes

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