Hydrochloric Acid → HCID 63897176, compound

HRID 714026Notes

Reaction equation

HRID 714026 reaction equation
S(Cl)(Cl)=O.[CH3:5][O:6][C:7]1[C:15]([O:16][CH3:17])=[CH:14][CH:13]=[CH:12][C:8]=1[C:9]([OH:11])=[O:10].CN(C=O)C.Cl>C1(C)C=CC=CC=1.CN(C)C1C=CN=CC=1.O.N1C=CC=CC=1>[CH3:5][O:6][C:7]1[C:15]([O:16][CH3:17])=[CH:14][CH:13]=[CH:12][C:8]=1[C:9]([O:11][C:8]([CH3:12])([CH3:9])[CH3:7])=[O:10]

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 152042,3-Dimethoxybenzoic acidHCID 24386Thionyl Chloride

Product 1

HCID 63897176HCID 63897176, compoundYield 166%

Reagents, catalysts & solvents 4

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 1049PyridineSolventHCID 1140TolueneSolvent

Conditions

Temperature
40 °C

Procedure

Add thionyl chloride (67.6 mL, 928 mmol) dropwise to a solution of 2,3-dimethoxybenzoic acid (132 g, 714 mmol) and DMF (1.32 mL) in toluene (528 mL) maintained at 40° C. Stir the solution for 1 h at 40° C. after the addition is complete. Concentrate the mixture in vacuo and dissolve the residue in dichloromethane (528 mL). Warm the mixture to reflux and add tert-butyl alcohol (203.4 mL). Add pyridine (86.6 mL) dropwise over 5 min followed by addition of N,N-dimethylpyridin-4-amine (4.36 g, 35.7 mmol) and stir the mixture 1 h while cooling to ambient temperature. Dilute the mixture with water (200 mL) and acidify the mixture (pH=2) with 2 N hydrochloric acid. Separate the phases and wash the organic phase with 0.5 N hydrochloric acid (2×30 mL). Wash the organic phase with 15% potassium carbonate, water, and brine. Concentrate the organic phase in vacuo to yield the title compound (141.2 g, 83%) as a white solid. ES/MS m/z 165 [M-(C4H9O)]+.

Workup

  1. additionafter the addition
  2. concentrationConcentrate the mixture in vacuo
  3. dissolutiondissolve the residue in dichloromethane (528 mL)
  4. temperatureWarm the mixture
  5. temperatureto reflux
  6. additionadd tert-butyl alcohol (203.4 mL)
  7. stirringstir the mixture 1 h
  8. temperaturewhile cooling to ambient temperature
  9. customSeparate the phases
  10. washwash the organic phase with 0.5 N hydrochloric acid (2×30 mL)
  11. washWash the organic phase with 15% potassium carbonate, water, and brine
  12. concentrationConcentrate the organic phase in vacuo

Sources & evidence

ORD record
ord-5310e1333d844538b6f32b4e1daa54de
Source dataset
uspto-grants-2015_11
Patent number
US09187411B2

Reaction notes

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