Formaldehyde → HCID 11523027, compound

HRID 215668Notes

Reaction equation

HRID 215668 reaction equation
[C:1]([BH3-])#[N:2].[Na+].[Br:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[O:12][C:11]([C:16]1[CH:21]=[CH:20][C:19](N)=[CH:18][CH:17]=1)=[CH:10][C:9]2=[O:23].[CH2:24]=O.[OH-].[Na+]>C(O)(=O)C>[Br:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[O:12][C:11]([C:16]1[CH:21]=[CH:20][C:19]([N:2]([CH3:1])[CH3:24])=[CH:18][CH:17]=1)=[CH:10][C:9]2=[O:23]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 115804956-bromo-4'-aminoflavone

Product 1

HCID 11523027HCID 11523027, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Sodium cyanoborohydride (74.5 mg, 1.19 mmol) was slowly added dropwise to an acetic acid solution (10 ml) that contained compound 5 (75 mg, 0.237 mmol) and paraformaldehyde (71.1 mg, 2.37 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-bromo-4′-dimethylaminoflavone (compound 7) in the form of a yellow crystal. Yield: 70 mg (yield constant: 85.7%) 1H NMR (300 MHz, CDCl3) δ8.34 (s, 1H), 7.72-7.82 (m, 3H), 7.43 (d, J=9.0 Hz, 1H), 6.70-6.77 (m, 3H), 3.08 (s, 6H). MS m/z 345 (M+).

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-8c94aca7404740288410b51c73e4a95f
Source dataset
uspto-grants-2012_06
Patent number
US08192717B2

Reaction notes

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