Ethyl 4,4,4-trifluoroacetoacetate → NSC282112

HRID 2398941Notes

Reaction equation

HRID 2398941 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH3:14])([CH3:13])[CH:7]([CH3:12])[N:8]2[CH3:11])=[CH:4][CH:3]=1.[F:15][C:16]([F:26])([F:25])[C:17](=O)[CH2:18][C:19](OCC)=[O:20]>>[O:20]=[C:19]1[CH:18]=[C:17]([C:16]([F:26])([F:25])[F:15])[C:3]2[C:2](=[CH:10][C:9]3[N:8]([CH3:11])[CH:7]([CH3:12])[C:6]([CH3:13])([CH3:14])[C:5]=3[CH:4]=2)[NH:1]1

Participants

3

Reactant 2

HCID 67793Ethyl 4,4,4-trifluoroacetoacetateHCID 118163411H-Indol-6-amine, 2,3-dihydro-1,2,3,3-tetramethyl-

Product 1

HCID 323233NSC282112

Procedure

6-Amino-1,2,3,3-tetramethylindoline (6.9 g, 0.036 mole) was treated with 6.8 g of ethyl trifluoroacetoacetate. There was an immediate reaction with heat evolution and formation of a solid. The mixture was heated in an oil bath under a reflux condenser for 16 hrs at 135°-140° C., then for 1 hr at 145°-150° C. The cooled cake was broken up, triturated with 10 ml of diethyl ether, filtered and washed twice with cold ether; 7.7 g (69%). When recrystallized from 275 ml of 95% ethanol, the compound was obtained as felted, yellow needles; m.p. 248°-249° C., shrinking at 244° C.

Workup

  1. customan immediate reaction
  2. temperaturewith heat evolution and formation of a solid
  3. temperatureThe mixture was heated in an oil bath under a reflux condenser for 16 hrs at 135°-140° C.
  4. customtriturated with 10 ml of diethyl ether
  5. filtrationfiltered
  6. washwashed twice with cold ether
  7. customWhen recrystallized from 275 ml of 95% ethanol
  8. customthe compound was obtained
  9. customshrinking at 244° C.

Sources & evidence

ORD record
ord-70500e96a89742a0b6711bd8abab8905
Source dataset
uspto-grants-1977_05
Patent number
US04026898

Reaction notes

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