HCID 86649422, compound → HCID 58765320, compound

HRID 2098091Notes

Reaction equation

HRID 2098091 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]([F:12])([F:11])[F:10])=[CH:4][C:3]=1/[CH:13]=[CH:14]/[C:15]([O:17]CC)=O>Cl.O1CCOCC1>[F:10][C:9]([F:12])([F:11])[O:8][C:5]1[CH:4]=[C:3]2[C:2](=[CH:7][CH:6]=1)[NH:1][C:15](=[O:17])[CH:14]=[CH:13]2

Participants

4

Reactant 1

HCID 86649422HCID 86649422, compound

Product 1

HCID 58765320HCID 58765320, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a stirring mixture of (E)-ethyl 3-(2-amino-5-(trifluoromethoxy)phenyl)acrylate (2.2 mmol) in 4N HCl in dioxane (25 mL) was added concentrated HCl (2 mL). The resulting mixture was warmed to 100° C. overnight. The reaction mixture was cooled to rt and then slowly quenched with a cold saturated NaHCO3 solution until pH>7. The product was extracted with EtOAc and used without further purification. Retention time (min)=1.804, method [1], MS (ESI) 230.1 (M+H).

Workup

  1. temperatureThe reaction mixture was cooled to rt
  2. customslowly quenched with a cold saturated NaHCO3 solution until pH>7
  3. extractionThe product was extracted with EtOAc
  4. customused without further purification

Sources & evidence

ORD record
ord-343e261e262c4cbe80d0a58c9aebb0a2
Source dataset
uspto-grants-2013_05
Patent number
US08450363B2

Reaction notes

Loading…