HCID 86649423, compound → HCID 68786833, compound

HRID 2098097Notes

Reaction equation

HRID 2098097 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([F:11])([F:10])[F:9])[C:3]=1/[CH:12]=[CH:13]/[C:14]([O:16]CC)=O>Cl.O1CCOCC1>[F:9][C:8]([F:11])([F:10])[C:4]1[CH:5]=[CH:6][CH:7]=[C:2]2[C:3]=1[CH:12]=[CH:13][C:14](=[O:16])[NH:1]2

Participants

4

Reactant 1

HCID 86649423HCID 86649423, compound

Product 1

HCID 68786833HCID 68786833, 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-6-(trifluoromethyl)phenyl)acrylate 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. A normal aqueous extraction with EtOAc was followed. The crude mixture was taken directly to the next reaction without further purification. Retention time (min)=1.892, method [1], MS (ESI) 214.0 (M+H).

Workup

  1. temperatureThe reaction mixture was cooled to rt
  2. customslowly quenched with a cold saturated NaHCO3 solution until pH>7
  3. extractionA normal aqueous extraction with EtOAc
  4. customThe crude mixture was taken directly to the next reaction without further purification

Sources & evidence

ORD record
ord-3eab1f7bd71f4803b71b706cba2c5e1c
Source dataset
uspto-grants-2013_05
Patent number
US08450363B2

Reaction notes

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