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

HRID 1604369Notes

Reaction equation

HRID 1604369 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%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of methyl 2-[N-(2-benzyloxy-5-bromobenzyl)-N-ethyl-amino]pyridine-5-carboxylate (10.0 g, 22 mmol) in dichloromethane (950 ml) was treated with boron trichloride dimethyl sulphide complex (40 ml, 2M, 80 mmol). The reaction was stirred at ambient temperature for 48 hours. Saturated aqueous sodium hydrogen carbonate solution was added and the layers were washed with dichloromethane. The organic layers were combined. dried (MgSO4) and evaporated to give an off white solid which was subjected to chromatography (eluant: ethyl acetate/hexane) to give methyl 2-[N-(5-bromo-2-hydroxybenzyl)-N-ethylamino]pyridine-5-carboxylate (6.02 g, 75%).

Workup

  1. washthe layers were washed with dichloromethane
  2. dry with materialdried (MgSO4)
  3. customevaporated
  4. customto give an off white solid which

Sources & evidence

ORD record
ord-c961e767c1e24ef1ab6a30899aed7564
Source dataset
uspto-grants-1999_11
Patent number
US05994353

Reaction notes

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