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

HRID 1455995Notes

Reaction equation

HRID 1455995 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+]>ClCCl>[OH: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]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 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-ethylamino]pyridine-5-carboxylate (10.0 g, 22 mmol) in dichloromethane (150 mL) was treated with trichloride dimethyl sulphide complex (40 ml, 2M, 80 mmol). The reaction was stirred at ambient temperature for 28 hours. Saturated aqueous sodium hydrogen carbonate solution was added and the layers separated. The aqueous layer was washed with dichloromethane, the organic layers combined, dried (MgSO4) and evaporated to give an off-white solid. This was subjected to chromatography to give methyl 2-[N-(2-hydroxy-5-bromobenzyl)-N-ethylamino]pyridine-5-carboxylate (6.0 g, 75%).

Workup

  1. customthe layers 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-f566066356aa40aeb4d1a0107b034dae
Source dataset
uspto-grants-1998_12
Patent number
US05843942

Reaction notes

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