m-Toluidine → HCID 89650571, compound

HRID 2174224Notes

Reaction equation

HRID 2174224 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[CH:3]=1.Cl[C:10]1[C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:14][N:13]=[C:12]([Cl:21])[CH:11]=1>Cl.C(O)C>[Cl:21][C:12]1[CH:11]=[C:10]([NH:1][C:2]2[CH:3]=[C:4]([CH3:8])[CH:5]=[CH:6][CH:7]=2)[C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:14][N:13]=1

Participants

5

Reactant 2

HCID 7934m-ToluidineHCID 600045Ethyl 4,6-dichloropyridine-3-carboxylate

Product 1

HCID 89650571HCID 89650571, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

(Wallace, E., et. al., ibid.) m-toluidine (0.47 mL, 4.34 mmol) and conc. HCl (1 drop) were added to a solution of compound iii (1.00 g, 4.57 mmol) in ethanol (10 mL). The reaction mixture was heated at 80° C. for 3 h, cooled to room temperature and partitioned between water (15 mL) and EtOAc (20 mL). The aqueous phase was extracted with EtOAc (3×20 mL). The combined organic phase was dried (MgSO4) and reduced in vacuo to give the crude product as a brown oil. Column chromatography (SiO2), eluting with 12:1 Hexanes-EtOAc, gave compound iv. (0.670 g, 2.31 mmol, 51%) as a light orange oil, which solidified on standing, [M+H]+ m/z=291.0.

Workup

  1. temperaturecooled to room temperature
  2. custompartitioned between water (15 mL) and EtOAc (20 mL)
  3. extractionThe aqueous phase was extracted with EtOAc (3×20 mL)
  4. dry with materialThe combined organic phase was dried (MgSO4)
  5. customto give the crude product as a brown oil
  6. washColumn chromatography (SiO2), eluting with 12:1 Hexanes-EtOAc

Sources & evidence

ORD record
ord-b1d8d2ff194548588bffd619f8a14bd7
Source dataset
uspto-grants-2015_06
Patent number
US09060515B2

Reaction notes

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