Sulfuric Acid → HCID 14390403, compound

HRID 2072972Notes

Reaction equation

HRID 2072972 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:16]([CH2:17][C:18]([OH:20])=[O:19])[C:11]3=[N:12][CH:13]=[CH:14][CH:15]=[C:10]3[N:9]=2)=[CH:4][CH:3]=1.[CH:21](O)([CH3:23])[CH3:22].S(=O)(=O)(O)O>C1C=CC=CC=1>[CH3:22][CH:21]([O:19][C:18](=[O:20])[CH2:17][N:16]1[C:11]2=[N:12][CH:13]=[CH:14][CH:15]=[C:10]2[N:9]=[C:8]1[C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)[CH3:23]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 3776IsopropanolHCID 143904574-chlorophenyl-3H-imidazo[4,5-b]pyridine-3-acetic acid

Product 1

HCID 14390403HCID 14390403, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 2-(4-chlorophenyl)-3H-imidazo[4,5-b]pyridine3-acetic acid (3.1 g, 0.0108 mole), isopropanol (50 ml), benzene (50 ml), and concentrated sulfuric acid (5 ml) was refluxed under a Dean-Stark trap for 24 hrs. The reaction mixture was concentrated and the residue partitioned between 5% potassium hydroxide solution (50 ml) and ethyl acetate (50 ml). The layers were separated and the aqueous portion extracted with ethyl acetate (2×25 ml). The organic layers were combined and washed with 5% potassium hydroxide (25 ml), water (25 ml), dried over sodium sulfate, and concentrated in vacuo to give 2.0 g (56%) of a solid, mp 118°-120° C. Recrystallization from isopropyl ether gave 1.7 g of off-white needles, mp 117.5°-119° C.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue partitioned between 5% potassium hydroxide solution (50 ml) and ethyl acetate (50 ml)
  3. customThe layers were separated
  4. extractionthe aqueous portion extracted with ethyl acetate (2×25 ml)
  5. washwashed with 5% potassium hydroxide (25 ml), water (25 ml)
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cf1d9256d7574156877f0eaf6bf38e60
Source dataset
uspto-grants-1990_04
Patent number
US04914109

Reaction notes

Loading…