Hydrochloric Acid → HCID 17871365, compound

HRID 1069111Notes

Reaction equation

HRID 1069111 reaction equation
C([O-])([O-])=O.[Cs+].[Cs+].[CH3:7][N:8]1[CH:12]=[CH:11][CH:10]=[C:9]1[C:13]([NH:15][C:16]1[CH:17]=[C:18]([CH:25]=[CH:26][CH:27]=1)/[CH:19]=[CH:20]/[C:21]([O:23]C)=[O:22])=[O:14].Cl>O.CO>[CH3:7][N:8]1[CH:12]=[CH:11][CH:10]=[C:9]1[C:13]([NH:15][C:16]1[CH:17]=[C:18]([CH:25]=[CH:26][CH:27]=1)/[CH:19]=[CH:20]/[C:21]([OH:23])=[O:22])=[O:14]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 10796Cesium carbonateHCID 86757056methyl (E)-3-(l-methylpyrrole-2-carboxamido)cinnamate

Product 1

HCID 17871365HCID 17871365, compoundYield 91.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of Cs2CO3 (3.26 g) in H2O (2 mL) was diluted with MeOH (8 mL) and ester 10 (0.91 g, 3.2 mmol) was added. The mixture was heated under reflux for 2.5 h then cooled and acidified with 0.5N HCl. The precipitated solid was collected, dried and dissolved in warm EtOAc. The solution was concentrated to a small volume under reduced pressure below 40° C. and then diluted with i-Pr2O to provide (E) -3- (1-methylpyrrole-2-carboxamido)cinnamic acid (11) (0.79 g, 91%) mp 202-204° C. 1H NMR [(CD3)2SO] δ12.44 (br s, 1 H, CO2H), 9.82 (s, 1 H, NH), 7.99 (s, 1 H, H-2), 7.79-7.73 (m, 1 H, H-4), 7.56 (d, J=16.0 Hz, 1 H, PhCH═CH), 7.40-7.34 (m, 2 H, H-5,6), 7.05 (dd, J=4.0, 1.7 Hz, 1 H, H-pyrrole), 7.02 (t, J=2.0 Hz, 1 H, H-pyrrole), 6.44 (d, J=16.0 Hz, 1 H, PhCH═CH), 6.11 (dd, J=3.8,2.6 Hz, 1 H, H-pyrrole), 3.89 (s, 3 H, NCH3).

Workup

  1. additionwas added
  2. temperatureThe mixture was heated
  3. temperatureunder reflux for 2.5 h
  4. temperaturethen cooled
  5. customThe precipitated solid was collected
  6. customdried
  7. dissolutiondissolved in warm EtOAc
  8. concentrationThe solution was concentrated to a small volume under reduced pressure below 40° C.
  9. additiondiluted with i-Pr2O

Sources & evidence

ORD record
ord-24b0e7157df14eb7bde4a3aec8705f60
Source dataset
uspto-grants-2001_06
Patent number
US06251933B1

Reaction notes

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