Sodium Hydroxide → HCID 178422884, compound

HRID 1178397Notes

Reaction equation

HRID 1178397 reaction equation
[NH:1]1[CH:5]=[C:4]([CH:6]=[C:7]2[C:16](=O)[C:15]3[N:14]=[C:13]([CH3:18])[CH:12]=[CH:11][C:10]=3[CH2:9][CH2:8]2)[N:3]=[CH:2]1.[H][H].Cl(O)(=O)(=O)=O.[OH-].[Na+]>FC(F)(F)C(O)=O.C(Cl)(Cl)Cl.C(O)(C)C.[Pt]=O>[NH:1]1[CH:5]=[C:4]([CH2:6][CH:7]2[CH2:16][C:15]3[N:14]=[C:13]([CH3:18])[CH:12]=[CH:11][C:10]=3[CH2:9][CH2:8]2)[N:3]=[CH:2]1

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 24247Perchloric AcidHCID 178418361HCID 178418361, compoundHCID 178422885HCID 178422885, compound2×

Product 1

HCID 178422884HCID 178422884, compound

Reagents, catalysts & solvents 3

HCID 82844Platinum oxide (PtO)CatalystHCID 6422Trifluoroacetic acidSolventHCID 21906603Chloroform isopropyl alcoholSolvent

Procedure

A mixture of 7-(1H-imidazol-4-yl-methylene)-2-methyl-6,7-dihydro-5H-quinolin-8-one (Intermediate 200A4) (23.8 g, 99 mmol) in trifluoroacetic acid (120 mL) was hydrogenated under 50 psi of hydrogen in the presence of 70% perchloric acid (8 mL) and platinum oxide (12 g) for 16 h at rt. The mixture was filtered through a bed of celite, washed with ethyl acetate and evaporated to leave a residue. The residue was diluted with chloroform:isopropanol (3:1), basified with 2 M NaOH and the aqueous layer was extracted with chloroform:isopropanol (3:1). The organic layers were pooled and evaporated to give the crude product. This material was purified by chromatography on SiO2 with 3 to 4% NH3-MeOH: CH2Cl2 to give 7-(1H-imidazol-4-ylmethyl)-2-methyl-5,6,7,8-tetrahydro-quinoline (Intermediate 200A5) as a slightly yellow solid, 5.16 g (23%).

Workup

  1. filtrationThe mixture was filtered through a bed of celite
  2. washwashed with ethyl acetate
  3. customevaporated
  4. customto leave a residue
  5. extractionthe aqueous layer was extracted with chloroform:isopropanol (3:1)
  6. customevaporated
  7. customto give the crude product
  8. customThis material was purified by chromatography on SiO2 with 3 to 4% NH3-MeOH

Sources & evidence

ORD record
ord-1edd5576521f487192a2154adc3e4327
Source dataset
uspto-grants-2007_10
Patent number
US07276522B2

Reaction notes

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