Water → HCID 86619938, compound

HRID 1716298Notes

Reaction equation

HRID 1716298 reaction equation
C([O:3][C:4](=O)[C:5]1[CH:10]=[C:9]([CH3:11])[CH:8]=[N:7][C:6]=1[Br:12])C.[H-].[H-].[H-].[H-].[Li+].[Al+3].CCOC(C)=O.O>CCOCC>[Br:12][C:6]1[C:5]([CH2:4][OH:3])=[CH:10][C:9]([CH3:11])=[CH:8][N:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 12919731Ethyl 2-bromo-5-methylpyridine-3-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 86619938HCID 86619938, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 2-bromo-5-methyl-nicotinic acid ethyl ester (0.4 g, 1.63 mmol) (synthesized according to Ponticello's procedure J. Org. Chem., 1978, 43, 2529-2535) in Et2O (10 mL) was dropwise added LiAlH4 (1.0 M in THF, 1.79 mL, 1.79 mmol) at −78° C. After the addition was completed, the suspension was stirred at −78 C for 1 h. EtOAc was carefully added at −78° C. and then water was dropwise added. The organic portion was brought to the usual work-up to give the product without further purification. 1H NMR (300 MHz, CDCl3) 8.13 (s, 1H), 7.68 (s, 1H), 4.73 (s, 2H), 2.33 (s, 3H).

Workup

  1. customat −78° C
  2. additionAfter the addition
  3. customto give the product
  4. customwithout further purification

Sources & evidence

ORD record
ord-117d6b285a2c42cfb831bf308d74857b
Source dataset
uspto-grants-2010_09
Patent number
US07803793B2

Reaction notes

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