Ethanol → Ethyl 6-hydroxy-5-iodonicotinate

HRID 1820980Notes

Reaction equation

HRID 1820980 reaction equation
[I:1][C:2]1[C:3]([OH:11])=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].S(=O)(=O)(O)O.[CH2:17](O)[CH3:18]>>[OH:11][C:3]1[C:2]([I:1])=[CH:10][C:6]([C:7]([O:9][CH2:17][CH3:18])=[O:8])=[CH:5][N:4]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 178524773HCID 178524773, compound

Product 1

HCID 178469850Ethyl 6-hydroxy-5-iodonicotinate

Procedure

A suspension of 4.6 g (17.36 mmol) of 5-iodo-6-hydroxynicotinic acid and 7.0 mL of concentrated sulfuric acid in 40 mL of ethanol was refluxed for 16 h. The reaction mixture was cooled to rt and filtered to afford 3.0 g of a white solid as the title compound: 1H NMR (500 MHz, DMSO) δ 1.25 (t, J=6.9, 3H), 4.21 (q, J=6.6, 2H), 8.05 (d, J=1.4, 1H), 8.33 (d, J=1.3, 1H).

Workup

  1. temperaturewas refluxed for 16 h
  2. filtrationfiltered

Sources & evidence

ORD record
ord-8e1841c5145a40f8b0eecb57dc0fb93c
Source dataset
uspto-grants-2009_10
Patent number
US07605171B2

Reaction notes

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