Trifluoroacetic acid → HCID 23346099, compound

HRID 1856207Notes

Reaction equation

HRID 1856207 reaction equation
[F:1][C:2]([F:24])([F:23])[C:3]([C:9]1[CH:10]=[C:11]2[C:16]3=[C:17]([CH2:19][CH2:20][N:15]3[C:14](=[O:21])[CH:13]=[C:12]2[CH3:22])[CH:18]=1)([OH:8])[C:4]([F:7])([F:6])[F:5].FC(F)(F)C(O)=O.[N+:32]([O-])([O-:34])=[O:33].[K+]>O>[F:5][C:4]([F:7])([F:6])[C:3]([C:9]1[CH:10]=[C:11]2[C:16]3=[C:17]([CH2:19][CH2:20][N:15]3[C:14](=[O:21])[C:13]([N+:32]([O-:34])=[O:33])=[C:12]2[CH3:22])[CH:18]=1)([OH:8])[C:2]([F:1])([F:23])[F:24]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 24434Potassium NitrateHCID 23346109HCID 23346109, compound

Product 1

HCID 23346099HCID 23346099, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred mixture of 7.0 g (0.02 mole) of 1,2-dihydro-8-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)-ethyl]-6-methyl-4H-pyrrolo[3,2,1-ij]quinolin-4-one and 70 ml of trifluoroacetic acid is added 4.2 g (0.042 mole) of potassium nitrate. The mixture is stirred for 16 hours at room temperature and then is refluxed for 30 minutes. The mixture is poured into 300 ml of water. The solid is filtered off, washed with water, and dried. Recrystallization from 250 ml of acetonitrile gives 3.3 g (42%) of 1,2-dihydro-8-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)-ethyl]-6-methyl-5-nitro-4H-pyrrolo[3,2,1-ij]quinolin-4-one, m.p. 289°-290° (dec).

Workup

  1. temperatureis refluxed for 30 minutes
  2. filtrationThe solid is filtered off
  3. washwashed with water
  4. customdried
  5. customRecrystallization from 250 ml of acetonitrile

Sources & evidence

ORD record
ord-6a1d6610f6474717a62848e27f82c4bf
Source dataset
uspto-grants-1980_08
Patent number
US04218448

Reaction notes

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