Sodium Hydroxide → HCID 56737040, compound

HRID 1468577Notes

Reaction equation

HRID 1468577 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([C:9]2[O:13][C:12]([CH:14]=[O:15])=[CH:11][CH:10]=2)=[C:4]([N+:16]([O-:18])=[O:17])[CH:3]=1.[OH-:19].[Na+]>[N+]([O-])([O-])=O.[Ag+].Cl>[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([C:9]2[O:13][C:12]([C:14]([OH:19])=[O:15])=[CH:11][CH:10]=2)=[C:4]([N+:16]([O-:18])=[O:17])[CH:3]=1

Participants

5

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 50851006HCID 50851006, compound

Product 1

HCID 56737040HCID 56737040, compound

Reagents, catalysts & solvents 2

HCID 24470Silver NitrateCatalystHCID 313Hydrochloric AcidSolvent

Conditions

Temperature
60 °C

Procedure

To 5-(4,5-dimethyl-2-nitrophenyl)furan-2-aldehyde (5a) (0.69 g, 2.81 mmol) was added solid NaOH (0.12 g, 3.09 mmol) and 10% NaOH solution (6.2 ml). Silver nitrate (0.47 g, 2.81 mmol) was added, and the reaction mixture heated to 60° C. for 3 h. After cooling to room temperature the resulting mixture was poured into 2N HCl (50 ml) during which the product precipitated out of solution and was collected by filtration. The crude solid was purified by column chromatography using 0-2% MeOH/DCM as eluent. (5i) was obtained yellow solid (41%). mp 231-233° C. 1H NMR (400 MHz, DMSO-d6): δ 2.34 and 2.35 (6H, 2s), 6.93 and 6.94 (dd, J=1.6 and 3.6 Hz, 1H), 7.31 and 7.32 (dd, J=1.2 and 3.2 Hz, 1H) 7.63 (s, 1H), 7.80 (s, 1H) 13.20 (brs, 1H); 13C NMR (100 MHz, DMSO-d6): δ 19.63, 19.84, 111.67, 120.01, 120.63, 125.62, 131.19, 140.48, 143.26, 145.82, 145.91, 152.59, 159.71; HRMS (m/z): [M+H]+ calcd for C13H12NO5, 262.0710; found, 262.0714.

Workup

  1. temperatureAfter cooling to room temperature the resulting mixture
  2. customprecipitated out of solution
  3. filtrationwas collected by filtration
  4. customThe crude solid was purified by column chromatography

Sources & evidence

ORD record
ord-1d7867fffc5a41b5ae2de9d8b4858381
Source dataset
uspto-grants-2015_04
Patent number
US09005670B2

Reaction notes

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