Trifluoroacetic acid → HCID 20375745, compound

HRID 1448808Notes

Reaction equation

HRID 1448808 reaction equation
COC1C=CC(COC([NH:11][CH:12]2[CH2:17][CH:16]=[CH:15][C:14]([C:18]([O:20][CH3:21])=[O:19])=[CH:13]2)=O)=CC=1.[F:24][C:25]([F:30])([F:29])[C:26]([OH:28])=[O:27]>C1(OC)C=CC=CC=1>[F:24][C:25]([F:30])([F:29])[C:26]([OH:28])=[O:27].[NH2:11][CH:12]1[CH2:17][CH:16]=[CH:15][C:14]([C:18]([O:20][CH3:21])=[O:19])=[CH:13]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 20375747HCID 20375747, compound

Product 1

HCID 20375745HCID 20375745, compound

Reagents, catalysts & solvents 1

HCID 7519AnisoleSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of 16.5 g of methyl 3-(p-methoxybenzyloxycarbonylamino)-1,5-cyclohexadienecarboxylate in 40 ml of anisole at about 25° C. is added slowly 30 ml of trifluoroacetic acid. After the addition of the first 5 ml the solid dissolves. The solution is cooled in a ice bath and the addition of trifluoroacetic acid continues. The solution is maintained at 0° C. for one hour, then the solvents are removed in vacuo (1 mm) maintaining the temperature below 40° C. The resulting oily residue is cooled to 0° C. and anhydrous ether added with stirring. The precipitate is filtered off to give 8.1 g of methyl 3-amino-1,5-cyclohexadienecarboxylate trifluoroacetate.

Workup

  1. dissolutiondissolves
  2. temperatureThe solution is cooled in a ice bath
  3. customthe solvents are removed in vacuo (1 mm)
  4. temperaturemaintaining the temperature below 40° C
  5. temperatureThe resulting oily residue is cooled to 0° C.
  6. additionanhydrous ether added
  7. filtrationThe precipitate is filtered off

Sources & evidence

ORD record
ord-d169a170d084436da7d5a967da676617
Source dataset
uspto-grants-1980_02
Patent number
US04187316

Reaction notes

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