Hydrochloric Acid → HCID 14328911, compound

HRID 867504Notes

Reaction equation

HRID 867504 reaction equation
C([N:8]1[CH:14]2[CH2:15][CH2:16][CH:9]1[CH2:10][N:11]([C:17]1[CH:26]=[C:25]3[C:20]([C:21](=[O:32])[C:22]([C:29]([OH:31])=[O:30])=[CH:23][N:24]3[CH2:27][CH3:28])=[CH:19][C:18]=1[F:33])[CH2:12][CH2:13]2)C1C=CC=CC=1.Cl.[H][H].C(Cl)(Cl)Cl>CO.[Pd].CCOCC>[CH2:27]([N:24]1[C:25]2[C:20](=[CH:19][C:18]([F:33])=[C:17]([N:11]3[CH2:12][CH2:13][CH:14]4[NH:8][CH:9]([CH2:16][CH2:15]4)[CH2:10]3)[CH:26]=2)[C:21](=[O:32])[C:22]([C:29]([OH:31])=[O:30])=[CH:23]1)[CH3:28]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 6212ChloroformHCID 14328910HCID 14328910, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 14328911HCID 14328911, compoundYield 19.3%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

7-(9-benzyl-3,9-diazabicyclo[4,2,1]non-3-yl)-6-fluoro-1-ethyl-1,4-dihydro-4-oxo-3-quinoline carboxylic acid (963 mg, 2.15 mmoles) was dissolved in 125 ml of methanol that was previously saturated with HCl. To this solution was added 1.25 g of 10% Pd/C and the mixture was treated with an atmosphere of 45 psi hydrogen on a Parr hydrogenation apparatus at 60° C. for 4.5 hours. The mixture was then cooled to room temperature and filtered of catalyst through a celite pad. The filtrate was stripped to dryness, taken up in water (50 ml) and the pH was adjusted to 7.0 with saturated sodium bicarbonate. This aqueous layer was extracted with three times 200 ml chloroform which was dried over sodium sulfate and evaporated to give a solid residue. This residue was taken up in a small amount of chloroform and ether from which crystallized an off-white material that was filtered and dried to give 149 mg (19.3%) of the title compound, m.p. 147°-150° C.

Workup

  1. filtrationfiltered of catalyst through a celite pad
  2. extractionThis aqueous layer was extracted with three times 200 ml chloroform which
  3. dry with materialwas dried over sodium sulfate
  4. customevaporated
  5. customto give a solid residue
  6. customcrystallized an off-white material that
  7. filtrationwas filtered
  8. customdried

Sources & evidence

ORD record
ord-3e0943bf6f554a56ad609b9df7bc9cea
Source dataset
uspto-grants-1988_10
Patent number
US04775668

Reaction notes

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