Sodium Bicarbonate → methyl 2-[N-(2-hydroxy-5-bromobenzyl)-N-ethylamino]pyridine-5-carboxylate

HRID 1870759Notes

Reaction equation

HRID 1870759 reaction equation
C([O:8][C:9]1[CH:28]=[CH:27][C:26]([Br:29])=[CH:25][C:10]=1[CH2:11][N:12]([C:15]1[CH:20]=[CH:19][C:18]([C:21]([O:23][CH3:24])=[O:22])=[CH:17][N:16]=1)[CH2:13][CH3:14])C1C=CC=CC=1.C(=O)(O)[O-].[Na+].C(OCC)(=O)C.CCCCCC>ClCCl>[Br:29][C:26]1[CH:27]=[CH:28][C:9]([OH:8])=[C:10]([CH:25]=1)[CH2:11][N:12]([C:15]1[CH:20]=[CH:19][C:18]([C:21]([O:23][CH3:24])=[O:22])=[CH:17][N:16]=1)[CH2:13][CH3:14]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 21226206Ethyl acetate hexaneHCID 22622546methyl 2-[N-(2-benzyloxy-5-bromobenzyl)-N-ethylamino]pyridine-5-carboxylate

Product 1

HCID 11728230methyl 2-[N-(2-hydroxy-5-bromobenzyl)-N-ethylamino]pyridine-5-carboxylateYield 75.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of methyl 2-[N-(2-benzyloxy-5-bromobenzyl)-N-ethylamino]-5-pyridylcarboxylate (10.0 g, 22 mM) in dichloromethane (150 ml) was treated with boron trichloride dimethyl sulfide complex (40 ml, 2M, 80 mM). The reaction was stirred at ambient temperature for 48 hours. Saturated sodium bicarbonate solution was added and the layers were separated. The aqueous layer was washed with dichloromethane. The organic layers were combined, dried (MgSO4) and evaporated to give an off-white solid. The off-white solid was subjected to chromatography (diluted with ethyl acetate/hexane) to give the title compound (6.02 g, 75%).

Workup

  1. customthe layers were separated
  2. washThe aqueous layer was washed with dichloromethane
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customto give an off-white solid

Sources & evidence

ORD record
ord-332729d378e847c4843a1e85ff18bba3
Source dataset
uspto-grants-2000_08
Patent number
US06100258

Reaction notes

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