Sodium borohydride → Ethyl 4-(3-chlorophenyl)-1,2-dihydro-6-[hydroxy(4-phenyl-2-thiazolyl)methyl]-2-oxo-3-quinolinecarboxylate

HRID 1830807Notes

Reaction equation

HRID 1830807 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([C:18]([C:20]4[S:21][CH:22]=[C:23]([C:25]5[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=5)[N:24]=4)=[O:19])[CH:16]=3)[NH:11][C:10](=[O:31])[C:9]=2[C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH:5]=[CH:6][CH:7]=1.[BH4-].[Na+]>CO.C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([CH:18]([OH:19])[C:20]4[S:21][CH:22]=[C:23]([C:25]5[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=5)[N:24]=4)[CH:16]=3)[NH:11][C:10](=[O:31])[C:9]=2[C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 22048464Ethyl 4-(3-chlorophenyl)-1,2-dihydro-2-oxo-6-[(4-phenyl-2-thiazolyl)carbonyl]-3-quinolinecarboxylate

Product 1

HCID 22048469Ethyl 4-(3-chlorophenyl)-1,2-dihydro-6-[hydroxy(4-phenyl-2-thiazolyl)methyl]-2-oxo-3-quinolinecarboxylateYield 81.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of intermediate (18) (0.0336 mol) in methanol (100 ml) and THF (100 ml) was cooled on an ice bath. Sodium tetrahydroborate (0.0336 mol) was added portionwise. The mixture was stirred at a low temperature for 30 min, then poured out into ice water and extracted with DCM. The organic layer was separated, dried (MgSO4), filtered and the solvent was evaporated till dryness. The residue was crystallized from 2-propanone/DIPE. The precipitate was filtered off and dried, yielding 14.2 g (81.6%) of ethyl 4-(3-chlorophenyl)-1,2-dihydro-6-[hydroxy(4-phenyl-2-thiazolyl)methyl]-2-oxo-3-quinolinecarboxylate (intermediate 19), mp. 127° C.

Workup

  1. temperaturewas cooled on an ice bath
  2. extractionextracted with DCM
  3. customThe organic layer was separated
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent was evaporated till dryness
  7. customThe residue was crystallized from 2-propanone/DIPE
  8. filtrationThe precipitate was filtered off
  9. customdried

Sources & evidence

ORD record
ord-c43c8d93a0204081b58f580a4abe4591
Source dataset
uspto-grants-2006_06
Patent number
US07067531B2

Reaction notes

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