Formaldehyde → HCID 25096969, compound

HRID 215678Notes

Reaction equation

HRID 215678 reaction equation
[C:1]([BH3-])#[N:2].[Na+].[CH3:5][O:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[O:13][C:12]([C:17]1[CH:22]=[CH:21][C:20](N)=[CH:19][CH:18]=1)=[CH:11][C:10]2=[O:24].[CH2:25]=O.[OH-].[Na+]>C(O)(=O)C>[CH3:5][O:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[O:13][C:12]([C:17]1[CH:22]=[CH:21][C:20]([N:2]([CH3:1])[CH3:25])=[CH:19][CH:18]=1)=[CH:11][C:10]2=[O:24]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 25096967HCID 25096967, compound

Product 1

HCID 25096969HCID 25096969, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Sodium cyanoborohydride (891 mg, 14.1 mmol) was slowly added to an acetic acid solution (30 ml) that contained compound 24 (630 mg, 2.36 mmol) and paraformaldehyde (707 mg, 23.6 mmol), while stirring. The obtained mixture was stirred at room temperature for 3 hours. After completion of the reaction, 50 ml of a 1 N sodium hydroxide aqueous solution was added to the reaction solution, and the obtained mixture was then extracted with 50 ml (25 ml×2) of chloroform. The extract was dried over anhydrous sodium sulfate, and the solvent was then distilled away under reduced pressure, so as to obtain a product of interest, 6-methoxy-4′-dimethylaminoflavone (compound 25) in the form of a yellow crystal. Yield: 450 mg (yield constant: 64.6%) 1H NMR (300 MHz, CDCl3) δ8.31 (s, 1H), 7.69-7.75 (m, 3H), 7.39 (d, J=8.7 Hz, 1H), 6.62-6.66 (m, 3H), 4.18 (s, 1H). 2.91 (s, 3H).

Workup

  1. stirringThe obtained mixture was stirred at room temperature for 3 hours
  2. additionwas added to the reaction solution
  3. extractionthe obtained mixture was then extracted with 50 ml (25 ml×2) of chloroform
  4. dry with materialThe extract was dried over anhydrous sodium sulfate
  5. distillationthe solvent was then distilled away under reduced pressure

Sources & evidence

ORD record
ord-d22757f724674dacb81582ff76eb38b8
Source dataset
uspto-grants-2012_06
Patent number
US08192717B2

Reaction notes

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