2,5-Difluoro-N-(1-methylethyl)benzamide → HCID 18678623, compound

HRID 1634813Notes

Reaction equation

HRID 1634813 reaction equation
[F:1][C:2]1[CH:13]=[CH:12][C:11]([F:14])=[CH:10][C:3]=1[C:4]([NH:6][CH:7]([CH3:9])[CH3:8])=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].CO.C(Cl)Cl>C1COCC1>[F:1][C:2]1[CH:13]=[CH:12][C:11]([F:14])=[CH:10][C:3]=1[CH2:4][NH:6][CH:7]([CH3:9])[CH3:8]

Participants

5

Reactant 3

HCID 176832992,5-Difluoro-N-(1-methylethyl)benzamideHCID 21226129Dichloromethane methanolHCID 21226445Aluminium lithium hydride

Product 1

HCID 18678623HCID 18678623, compoundYield 64.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2,5-Difluoro-N-isopropyl-benzamide (0.5 g, 0.0025 mol) was dissolved in THF (8 mL). Lithium aluminum hydride (8 mL of a 1M solution in THF) was added, and the reaction was heated at reflux. When complete by TLC (methanol/methylene chloride), the reaction was cooled, and quenched with water, aqueous NaOH (15%), water and Na2SO4. The white solid is filtered off, and the filtrate is concentrated in vacuo to give 0.3 g of the amine. The product was used in the next step without characterization.

Workup

  1. temperaturethe reaction was heated
  2. temperatureat reflux
  3. customquenched with water, aqueous NaOH (15%), water and Na2SO4
  4. filtrationThe white solid is filtered off
  5. concentrationthe filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-390036e78f55464baaadaf73e19244b1
Source dataset
uspto-grants-2003_01
Patent number
US06506901B2

Reaction notes

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