Sodium borohydride → Ethyl 1-(4-fluorophenyl)-6-(hydroxymethyl)-4-oxo-1,4-dihydroquinoline-3-carboxylate

HRID 1048877Notes

Reaction equation

HRID 1048877 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:17]3[C:12](=[CH:13][C:14]([CH:18]=[O:19])=[CH:15][CH:16]=3)[C:11](=[O:20])[C:10]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:9]2)=[CH:4][CH:3]=1.[BH4-].[Na+]>C(O)C.CCOC(C)=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:17]3[C:12](=[CH:13][C:14]([CH2:18][OH:19])=[CH:15][CH:16]=3)[C:11](=[O:20])[C:10]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:9]2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 121447931Ethyl 1-(4-fluorophenyl)-6-formyl-4-oxo-1,4-dihydroquinoline-3-carboxylate

Product 1

HCID 121447982Ethyl 1-(4-fluorophenyl)-6-(hydroxymethyl)-4-oxo-1,4-dihydroquinoline-3-carboxylateYield 57%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To compound H (335 mg, 0.99 mmol) in ethanol (5 mL) cooled to 0° C. was added sodium borohydride (18.7 mg, 0.49 mmol). After ten minutes, the reaction was diluted with EtOAc and washed well with water. The organic layer was dried (MgSO4), filtered and concentrated in vacuo. Purification by flash chromatography on silica gel afforded 192 mg (57%) of the title compound. 1H NMR (400 MHz, DMSO-d6) δ 8.44 (s, 1H), 8.25 (s, 1H), 7.76-7.72 (m, 2H), 7.61 (d, J=6 Hz, 1H), 7.54 (t, J=8.64, 8.68 Hz, 2H), 6.94 (d, J=8.68, 1H), 5.42 (t, J=5.68, 5.64 Hz, 1H), 4.62 (d, J=5.48 Hz, 2H), 4.23 (q, J=7.08 Hz, 2H), 1.27 (t, J=7.12, 7.04 Hz, 3H); ES-MS [M+1]+: 342.3.

Workup

  1. waitAfter ten minutes
  2. washwashed well with water
  3. dry with materialThe organic layer was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by flash chromatography on silica gel

Sources & evidence

ORD record
ord-08378c69e8854f3bae8610197e69c2ce
Source dataset
uspto-grants-2016_07
Patent number
US09382208B1

Reaction notes

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