Trifluoroacetic acid → HCID 18997003, compound

HRID 374643Notes

Reaction equation

HRID 374643 reaction equation
FC(F)(F)C(OC(=O)C(F)(F)F)=O.[CH3:14][O:15][C:16]1[C:29]2[C:28](=[O:30])[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][C:26]=3[O:31][CH3:32])[C:21](=[O:33])[C:20]=2[CH:19]=[C:18]([CH:34]=[N:35]O)[CH:17]=1.FC(F)(F)C(O)=O>N1C=CC=CC=1.O1CCOCC1>[CH3:14][O:15][C:16]1[C:29]2[C:28](=[O:30])[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][C:26]=3[O:31][CH3:32])[C:21](=[O:33])[C:20]=2[CH:19]=[C:18]([C:34]#[N:35])[CH:17]=1

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 9845Trifluoroacetic anhydride2×HCID 73504046HCID 73504046, compound

Product 1

HCID 18997003HCID 18997003, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
65 °C

Procedure

Trifluoroacetic anhydride (4.62 ml, 6.87 g), was added dropwise with magnetic stirring to a suspension of 9,10-dihydro-4,5-dimethoxy-9,10-dioxoanthracene-2-aldoxime (10.74 ml, 9.24 g) in pyridine (10.5 ml, 10.336 g) and dioxan (100 ml) at room temperature under nitrogen. The temperature rose from 23° C. to 31° C. The mixture was then heated at 65° C. for 2 hours. More trifluoroacetic anhydride (4.62 ml, 6.87 g) was added at 65° C. and the mixture was stirred for a further 1 hour at 65° C. More trifluoroacetic acid (1 ml, 1.487 g) was added and the mixture stirred for 16 hours at 65° C., cooled, filtered, washed with water (200 ml) and dried in vacuo at 70° C. to give the nitrile, m.p. 266°-268° C.

Workup

  1. customrose from 23° C. to 31° C
  2. stirringthe mixture stirred for 16 hours at 65° C.
  3. temperaturecooled
  4. filtrationfiltered
  5. washwashed with water (200 ml)
  6. customdried in vacuo at 70° C.

Sources & evidence

ORD record
ord-cb8a7fe71cff49b4b3137612d0e175e6
Source dataset
uspto-grants-1996_01
Patent number
US05480873

Reaction notes

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