Dimethylformamide → HCID 23346124, compound

HRID 1856213Notes

Reaction equation

HRID 1856213 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].[CH3:25]N(C)C=O.CC(C)([O-])C.[K+].S(OC)(OC)(=O)=O>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])[CH:13]=[C:12]2[CH3:22])[CH:18]=1)([O:8][CH3:25])[C:2]([F:1])([F:23])[F:24]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6497Dimethyl SulfateHCID 23346109HCID 23346109, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 23346124HCID 23346124, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred mixture of 3.5 g 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 20 ml of dry dimethylformamide is added 1.3 g (0.012 mole) of potassium tert-butoxide in a dry nitrogen atmosphere. The mixture is heated gently to 100° and is allowed to cool. Then 1 ml (1.35 g, 0.011 mole) of dimethyl sulfate is added, and the mixture is warmed gently to 100°. The mixture is allowed to cool to room temperature and is poured into 100-200 ml of water. The precipitate is filtered off and then is triturated with 10% sodium hydroxide solution. The insoluble material is filtered off, washed with water, and dried. Recrystallization from alcohol gives 1.8 g (49%) of 1,2-dihydro-8-[2,2,2-trifluoro-1-methoxy-1-(trifluoromethyl)-ethyl]-6-methyl-4H-pyrrolo[3,2,1-ij]quinolin-4-one, m.p. 242°-243°.

Workup

  1. temperatureThe mixture is heated gently to 100°
  2. temperatureto cool
  3. temperaturethe mixture is warmed gently to 100°
  4. filtrationThe precipitate is filtered off
  5. customis triturated with 10% sodium hydroxide solution
  6. filtrationThe insoluble material is filtered off
  7. washwashed with water
  8. customdried
  9. customRecrystallization from alcohol

Sources & evidence

ORD record
ord-e70fefe9f48246e7bacd7da34c5414eb
Source dataset
uspto-grants-1980_08
Patent number
US04218448

Reaction notes

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