HCID 23346122, compound → HCID 23346123, compound

HRID 1856212Notes

Reaction equation

HRID 1856212 reaction equation
Cl[C:2]1[C:3]2[CH:15]=[C:14]([C:16]([OH:25])([C:21]([F:24])([F:23])[F:22])[C:17]([F:20])([F:19])[F:18])[CH:13]=[C:5]3[CH2:6][CH2:7][CH2:8][N:9]([C:10](=[O:12])[CH:11]=1)[C:4]=23.O.O.O.C([O-])(=O)C.[Na+]>[Pd].C(O)(=O)C>[F:24][C:21]([F:22])([F:23])[C:16]([C:14]1[CH:13]=[C:5]2[C:4]3[N:9]([CH2:8][CH2:7][CH2:6]2)[C:10](=[O:12])[CH:11]=[CH:2][C:3]=3[CH:15]=1)([OH:25])[C:17]([F:20])([F:19])[F:18]

Participants

5

Reactant 2

HCID 23346122HCID 23346122, compoundHCID 23665404Sodium Acetate Trihydrate

Product 1

HCID 23346123HCID 23346123, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 0.7 g. of 7-chloro-2,3-dihydro-9-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]-1H,5H-benzo[ij]quinolizin-5-one, 150 ml. of glacial acetic acid, 5 g. of sodium acetate trihydrate, and 0.5 g. of 10% palladium on charcoal is hydrogenated in a Parr shaker apparatus for 4 hours at an initial pressure of 3 atm. The catalyst is removed by filtration, solvent is removed by evaporation, and the residue is triturated with water. The insoluble material is filtered off, dried and recrystallized to give 2,3-dihydro-9-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]-1H,5H-benzo[ij]quinolizin-5-one, m.p. 295°-296°.

Workup

  1. additionA mixture of 0.7 g
  2. customThe catalyst is removed by filtration, solvent
  3. customis removed by evaporation
  4. customthe residue is triturated with water
  5. filtrationThe insoluble material is filtered off
  6. customdried
  7. customrecrystallized

Sources & evidence

ORD record
ord-c73989dcbd434e48a84a27e0077714d1
Source dataset
uspto-grants-1980_08
Patent number
US04218448

Reaction notes

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