Sodium Hydroxide → HCID 23081559, compound

HRID 1932429Notes

Reaction equation

HRID 1932429 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:19][CH2:18][CH:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:11][CH2:10]2)=[CH:5][CH:4]=1.B(Br)(Br)Br.[OH-].[Na+]>ClCCl>[OH:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:10][CH2:11][CH:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:18][CH2:19]2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 25134Boron tribromideHCID 68525969HCID 68525969, compound

Product 1

HCID 23081559HCID 23081559, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of ethyl N-(4-methoxyphenyl)-isonipecotate (2.63 g, 10 mmol) in dichloromethane (100 mL) was added a solution of 2 M boron tribromide in dichloromethane (20 mL, 40 mmol), and the resulting solution was stirred for 0.5 hours at room temperature. The resulting reaction solution was poured into ice water, then an aqueous solution of 1 M sodium hydroxide (110 mL) was added to the solution. After stirring, the resulting solution was separated. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and evaporated under reduced pressure to thereby yield 2.43 g of the title compound.

Workup

  1. customThe resulting reaction solution
  2. stirringAfter stirring
  3. customthe resulting solution was separated
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated under reduced pressure to thereby yield 2.43 g of the title compound

Sources & evidence

ORD record
ord-4a8b9cf8811645dabdc5c815a60b075a
Source dataset
uspto-grants-2012_05
Patent number
US08188277B2

Reaction notes

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