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Water → 2-(Benzo[2,1,3]oxadiazol-5-yloxy)-nicotinic acid ethyl ester

HRID 350967
Notes
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Reaction equation

HRID 350967 reaction equation
[CH2:1]([O:3][C:4](=[O:12])[C:5]1[CH:10]=[CH:9][CH:8]=[N:7][C:6]=1Cl)[CH3:2].[OH:13][C:14]1[CH:15]=[CH:16][C:17]2[C:18]([CH:22]=1)=[N:19][O:20][N:21]=2.C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C)C=O>[CH2:1]([O:3][C:4](=[O:12])[C:5]1[CH:10]=[CH:9][CH:8]=[N:7][C:6]=1[O:13][C:14]1[CH:15]=[CH:16][C:17]2=[N:21][O:20][N:19]=[C:18]2[CH:22]=1)[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 2796614Ethyl chloronicotinateHCID 1354568365-Hydroxybenzofurazan

Product 1

HCID 235293452-(Benzo[2,1,3]oxadiazol-5-yloxy)-nicotinic acid ethyl esterYield 26.2%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Conditions

Temperature
90 °C

Procedure

A mixture of 5.5 g (29.4 mmol.) 2-chloro nicotinic acid ethyl ester, 4.0 g (29.4 mmol.) 5-hydroxybenzofurazan and 20.1 g (61.7 mmol.) cesium carbonate in 125 ml dry dimethylforamide was heated at 90° C. for five days. The mixture was poured into water and extracted with ethyl acetate. The ethyl acetate extracts were combined, washed successively with sodium bicarbonate solution, water, brine then dried (Na2SO4) and concentrated in vacuo to give a solid. Recrystallization from diethyl ether/pentane gave 2.2 g (26%) solid.

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed successively with sodium bicarbonate solution, water, brine
  3. dry with materialthen dried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customto give a solid
  6. customRecrystallization from diethyl ether/pentane

Sources & evidence

ORD record
ord-931a482587134672be1326ce3172d68f
Source dataset
uspto-grants-2007_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07183293B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes