Ammonium Chloride → HCID 20145726, compound

HRID 1670724Notes

Reaction equation

HRID 1670724 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][N:3]=1.[C:10]1([Mg]Br)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[Cl-].[NH4+]>O1CCCC1>[Cl:1][C:2]1[N:3]=[CH:4][C:5]([CH:6]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[OH:7])=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 27640536-Chloropyridine-3-carbaldehydeHCID 178418255HCID 178418255, compound

Product 1

HCID 20145726HCID 20145726, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 6-chloronicotinaldehyde (1.0 g, 7.1 mmol) in anhydrous tetrahydrofuran (10 mL) was added phenylmagnesium bromide solution (3M in diethyl ether, 2.6 mL, 7.8 mmol) dropwise at −78° C. under argon. After the reaction mixture was stirred at −78° C. for 10 min and 0° C. for 20 min, saturated aqueous ammonium chloride solution (10 mL) was added to quench the reaction. The mixture was extracted with ethyl acetate (3×10 mL). The combined ethyl acetate extracts were dried (Na2SO4) and concentrated to give (6-chloropyridin-3-yl)(phenyl)methanol (1.5 g, 6.8 mmol, 96% yield) as a yellow liquid. MS found: (M+H)+=220.09.

Workup

  1. customto quench
  2. customthe reaction
  3. extractionThe mixture was extracted with ethyl acetate (3×10 mL)
  4. dry with materialThe combined ethyl acetate extracts were dried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-6b70dcf89c874107a4867c1fca43995b
Source dataset
uspto-grants-2011_08
Patent number
US07994190B2

Reaction notes

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