Hydrochloric Acid → HCID 66545108, compound

HRID 1948365Notes

Reaction equation

HRID 1948365 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]([N+:11]([O-:13])=[O:12])=[CH:9][N:10]=1)[C:5]([OH:7])=[O:6].[CH2:14](C(CC)(CC)C([O-])([O-])[O-])[CH3:15].Cl>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]([N+:11]([O-:13])=[O:12])=[CH:9][N:10]=1)[C:5]([O:7][CH2:14][CH3:15])=[O:6]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 184406222-Chloro-5-nitroisonicotinic acid2×HCID 21875354Triethylorthoaceate

Product 1

HCID 66545108HCID 66545108, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 2-chloro-5-nitroisonicotinic acid (Intermediate 208) and 16 ml triethylorthoacetate in 100 ml toluene was heated at reflux for 2 h. The mixture as stirred with 1N HCl for 30 min before being partitioned between EtOAc and water. The EtOAc was separated, washed with water and brine, dried (MgSO4) and concentrated. Chromatographed on silica gel (100% hexanes with gradient elution to 100% CH2Cl2 to give product as an oil. MS (ES) (MH+): 231 for C8H7ClN2O4; NMR (d6-DMSO): 1.3 (t, 3H), 4.4 (m, 2H), 8.1 (s, 1H), 9.2 (s, 1H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 h
  3. custombefore being partitioned between EtOAc and water
  4. customThe EtOAc was separated
  5. washwashed with water and brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customChromatographed on silica gel (100% hexanes
  9. washwith gradient elution to 100% CH2Cl2
  10. customto give product as an oil

Sources & evidence

ORD record
ord-af78b878899c4fb4ac712f90246bfe00
Source dataset
uspto-grants-2013_03
Patent number
US08399489B2

Reaction notes

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