m-Toluidine → HCID 970847, compound

HRID 1986156Notes

Reaction equation

HRID 1986156 reaction equation
[Cl:1][C:2]1[CH:10]=[C:6]([C:7]([OH:9])=O)[C:5]([OH:11])=[CH:4][CH:3]=1.[NH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[CH:14]=1.O(CC)P(OP(OCC)OCC)OCC>C1(C)C=CC=CC=1.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:11])=[C:6]([CH:10]=1)[C:7]([NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[CH:14]=1)=[O:9]

Participants

6

Reactant 3

HCID 7934m-ToluidineHCID 94475-Chlorosalicylic AcidHCID 88987Tetraethyl pyrophosphite

Product 1

HCID 970847HCID 970847, compoundYield 26.9%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 5-Chlorosalicylic acid (0.338 g, 1.9 mmol), m-Toluidine (0.2 g, 1.9 mmol) and Tetraethyl pyrophosphite (0.53 g, 2.0 mmol) in dry toluene was refluxed 7 hrs under nitrogen atmosphere. It was diluted with ethyl acetate, washed with HCl (10%) and then with water (3×30 mL). The organic layer was dried (Na2SO4), filtered and evaporated under vacuum. The resulting crude material was purified by column chromatography over SiO2 using mixture of ethyl acetate and hexanes (2:8) to give title compound (0.134 g,) 1H NMR (CDCl3/DMSO-d6) δ 2.38 (s, 3H), 6.89-7.03 (m, 2H), 7.19-7.59 (m, 4H), 8.08 (d, 1H), 9.92 (bs, 1H), 12.05 (s, 1H).

Workup

  1. temperaturewas refluxed 7 hrs under nitrogen atmosphere
  2. washwashed with HCl (10%)
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated under vacuum
  6. customThe resulting crude material was purified by column chromatography over SiO2 using mixture of ethyl acetate and hexanes (2:8)

Sources & evidence

ORD record
ord-7daef3dbf7db4d3292b191d9ff1ab942
Source dataset
uspto-grants-2009_06
Patent number
US07547804B2

Reaction notes

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