Ethyl Acetate → HCID 59773503, compound

HRID 2114298Notes

Reaction equation

HRID 2114298 reaction equation
FC(F)(F)C(O)=O.[NH2:8][CH2:9][C:10]([N:12]([CH3:19])[C:13]1[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=1)=O.[H-].[H-].[H-].[H-].[Li+].[Al+3].C(OCC)(=O)C>C1COCC1>[CH3:19][N:12]([C:13]1[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=1)[CH2:10][CH2:9][NH2:8]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 21226445Aluminium lithium hydrideHCID 69153779HCID 69153779, compound

Product 1

HCID 59773503HCID 59773503, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
70 °C

Procedure

2-Amino-N-methyl-N-pyridin-4-yl-acetamide trifluoroacetate (182, 1.0 eq.) was dissolved in anhydrous THF (50 mL) under argon. A 1 M solution of LiAlH4 in THF (6.1 eq.) was added dropwise at rt and the reaction vessel was placed in an oil bath. The temperature was raised to 70° C. and the mixture stirred for 15 hr. The reaction mixture was cooled and quenched by the slow addition of water (5 mL). Solvents were evaporated to give a white solid which was titurated several times with ethyl acetate to give compound 183 as a colourless oil.

Workup

  1. customthe reaction vessel was placed in an oil bath
  2. temperatureThe reaction mixture was cooled
  3. customquenched by the slow addition of water (5 mL)
  4. customSolvents were evaporated
  5. customto give a white solid which

Sources & evidence

ORD record
ord-f67c122d367f4734b78dfadb70625dca
Source dataset
uspto-grants-2008_10
Patent number
US07432379B2

Reaction notes

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