Formaldehyde → HCID 11716918, compound

HRID 215667Notes

Reaction equation

HRID 215667 reaction equation
[CH3:1][O-].[Na+].CO.[Br: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]([NH2:23])=[CH:19][CH:18]=1)=[CH:11][C:10]2=[O:24].C=O.[BH4-].[Na+]>CO>[Br: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]([NH:23][CH3:1])=[CH:19][CH:18]=1)=[CH:11][C:10]2=[O:24]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 4311764Sodium borohydrideHCID 115804956-bromo-4'-aminoflavoneHCID 23694274Sodium methanolate methanol

Product 1

HCID 11716918HCID 11716918, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A sodium methylate-methanol solution (0.27 ml) was slowly added dropwise to a methanol solution (15 ml) that contained compound 5 (300 mg, 0.949 mmol) and paraformaldehyde (154 mg, 5.13 mmol), while stirring. The obtained mixture was heated to reflux for 1 hour. Thereafter, sodium borohydride (180 mg, 4.75 mmol) that was in the form of a solid was added to the reaction solution by slow degrees, and the obtained mixture was further heated to reflux for 2 hours. Thereafter, the reaction solvent was distilled away under reduced pressure, and the residue was then subjected to silica gel column chromatography using ethyl acetate/hexane (3/5) as an elution solvent, so as to obtain a product of interest, 6-bromo-4′-methylaminoflavone (compound 6). Yield: 121 mg (yield constant: 38.6%) 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. temperatureThe obtained mixture was heated
  2. temperatureto reflux for 1 hour
  3. additionwas added to the reaction solution by slow degrees
  4. temperaturethe obtained mixture was further heated
  5. temperatureto reflux for 2 hours
  6. distillationThereafter, the reaction solvent was distilled away under reduced pressure

Sources & evidence

ORD record
ord-2a413a9707f14267b3b5be4dba6b1434
Source dataset
uspto-grants-2012_06
Patent number
US08192717B2

Reaction notes

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