Hydrochloric Acid → HCID 178505585, compound

HRID 735438Notes

Reaction equation

HRID 735438 reaction equation
F[C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:5]=[CH:4][C:3]=1[C:12]([C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=1)=O.O.[NH2:22][NH2:23].CCOC(C)=O.Cl>N1C=CC=CC=1.CN(C)C1C=CN=CC=1>[F:20][C:17]1[CH:18]=[CH:19][C:14]([C:12]2[C:3]3[C:2](=[C:7]([C:8]([F:11])([F:10])[F:9])[CH:6]=[CH:5][CH:4]=3)[NH:23][N:22]=2)=[CH:15][CH:16]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 24654Hydrazine hydrate (1:1)HCID 25149910(2-Fluoro-3-trifluoromethyl-phenyl)-(4-fluoro-phenyl)-methanone

Product 1

HCID 178505585HCID 178505585, compoundYield 80.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Conditions

Temperature
110 °C

Procedure

(2-Fluoro-3-trifluoromethyl-phenyl)-(4-fluoro-phenyl)-methanone (6.58 g, 23 mmol) was dissolved in 20 ml of pyridine. Hydrazine hydrate (7.36 mL, 230 mmol) and 4-(dimethylamino)-pyridine (2.8 g, 23 mmol) were added. The reaction mixture was stirred overnight at 110° C. After cooling to room temperature, EtOAc and 2N HCl were added. The organic phase was washed three times with brine, dried over NaSO4 and concentrated under vacuum. Purification of the crude product by plug filtration (silica gel, CH2Cl2) provided 5.18 g product as a white solid.

Workup

  1. temperatureAfter cooling to room temperature
  2. washThe organic phase was washed three times with brine
  3. dry with materialdried over NaSO4
  4. concentrationconcentrated under vacuum
  5. customPurification of the crude product
  6. filtrationby plug filtration (silica gel, CH2Cl2)

Sources & evidence

ORD record
ord-8567f69c9d714ac0b1963bd0f4de88d7
Source dataset
uspto-grants-2009_09
Patent number
US07592363B2

Reaction notes

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