Sodium Chlorite → HCID 67405349, compound

HRID 1056878Notes

Reaction equation

HRID 1056878 reaction equation
[O-:1]Cl=O.[Na+].[CH2:5]([O:12][C:13]1[C:14](=[O:33])[CH:15]=[C:16]([CH:31]=[O:32])[N:17]([C:19]2[CH:20]=[C:21]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH:22]=[CH:23][CH:24]=2)[CH:18]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>CC(C)=O.O>[CH2:5]([O:12][C:13]1[C:14](=[O:33])[CH:15]=[C:16]([C:31]([OH:1])=[O:32])[N:17]([C:19]2[CH:20]=[C:21]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH:22]=[CH:23][CH:24]=2)[CH:18]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 2

HCID 23668197Sodium ChloriteHCID 86680272HCID 86680272, compound

Product 1

HCID 67405349HCID 67405349, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

NaClO2 (28.3 g, 315 mmol) was added portion-wise to a mixture of 5-(benzyloxy)-1-(biphenyl-3-yl)-4-oxo-1,4-dihydropyridine-2-carbaldehyde (80 g, 210 mmol) in 800 mL of acetone and 800 mL of water at room temperature. The resulting mixture was stirred at room temperature for 3 h. The solvent was removed to give a residue which was washed with water and MeOH and dried to give 5-(benzyloxy)-1-(biphenyl-3-yl)-4-oxo-1,4-dihydropyridine-2-carboxylic acid. ′H NMR δ (400 MHz, d6-OMSO): 7.79 (s, 1H), 7.77-7.68 (m, 4H), 7.57 (t, J=8.0 Hz, 1H), 7.48 (t, =7.6 Hz, 2H), 7.42-7.31 (m, 7H), 6.66 (s, 1H), 5.04 (s, 2H).

Workup

  1. customThe solvent was removed
  2. customto give a residue which
  3. washwas washed with water and MeOH
  4. customdried

Sources & evidence

ORD record
ord-10cd98fab83f4761a0afac0cf5d87192
Source dataset
uspto-grants-2016_07
Patent number
US09399651B2

Reaction notes

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