Hydrochloric Acid → HCID 21250069, compound

HRID 1416944Notes

Reaction equation

HRID 1416944 reaction equation
FC(F)(F)C(OC(=O)C(F)(F)F)=[O:4].[CH2:14]([N:21]([CH3:43])[C:22]([C:24]1[CH:37]=[N:36][C:35]2[C:26](=[CH:27][C:28]([F:42])=[C:29]3[C:34]=2[N:33]=[CH:32][C:31]([C:38](=O)[NH2:39])=[C:30]3Cl)[CH:25]=1)=[O:23])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.Cl>N1C=CC=CC=1>[CH2:14]([N:21]([CH3:43])[C:22]([C:24]1[CH:37]=[N:36][C:35]2[C:26](=[CH:27][C:28]([F:42])=[C:29]3[C:34]=2[N:33]=[CH:32][CH:31]([C:38]#[N:39])[C:30]3=[O:4])[CH:25]=1)=[O:23])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 9845Trifluoroacetic anhydrideHCID 21250047HCID 21250047, compound

Product 1

HCID 21250069HCID 21250069, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Trifluoroacetic anhydride (0.5 ml) was added dropwise to a stirred, ice-cooled mixture of 8-(N-benzyl-N-methylcarbamoyl)-3-carbamoyl-4-chloro-5-fluoro-1,10-phenanthroline (0.3 g) in pyridine (3 ml). The mixture was stirred at ambient temperature for 1 hour. The mixture was acidified with 3M hydrochloric acid and stirred at ambient temperature for 18 hours. The mixture was filtered and the solid so obtained recrystallised from a mixture of methanol and ethyl acetate to give 8-(N-benzyl-N-methylcarbamoyl)-3-cyano-5-fluoro-4-oxo-3,4-dihydro-1,10-phenanthroline in 24% yield, mp 267-269° C.

Workup

  1. temperaturecooled
  2. stirringstirred at ambient temperature for 18 hours
  3. filtrationThe mixture was filtered
  4. customthe solid so obtained
  5. customrecrystallised from a mixture of methanol and ethyl acetate

Sources & evidence

ORD record
ord-1db6c1a4657b4bcaac12e13a8ab42179
Source dataset
uspto-grants-1999_06
Patent number
US05916898

Reaction notes

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