Dimethylamine → HCID 44608333, compound

HRID 388207Notes

Reaction equation

HRID 388207 reaction equation
[CH3:1][O:2][C:3]1[C:4]([OH:21])=[CH:5][C:6]([OH:20])=[C:7]2[C:12](=[O:13])[CH:11]=[C:10]([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[O:9][C:8]=12.[CH2:22]=O.[CH3:24][NH:25][CH3:26]>CO>[CH3:24][N:25]([CH2:22][C:5]1[C:6]([OH:20])=[C:7]2[C:8](=[C:3]([O:2][CH3:1])[C:4]=1[OH:21])[O:9][C:10]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[CH:11][C:12]2=[O:13])[CH3:26]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 712FormaldehydeHCID 5281703Wogonin

Product 1

HCID 44608333HCID 44608333, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
55 °C

Procedure

The mixture of Wogonin (28.4 g), methanol (350 ml), 37% formaldehyde solution (8.1 ml), 33% dimethylamine solution (13.6 g) was stirred under for 4 hours at 55° C., then precipitates were removed by filtration and washed several times with methanol, after drying under reduced pressure at 65° C. to get the product as yellow solid 32.7 g of purity 99.3%. MS: (API-ES) m/z 342.5[M+H]+; 1H NMR (DMSO-d6, 400 MHz) δ 8.03˜8.04 (m, 2H, Ar-2′,6′-H), 7.59-7.60 (m, 3H, Ar-3′,4′,5′-H), 6.81 (s, 1H, 3-H), 3.97 (s, 2H, CH2), 3.82 (s, 3H, 8-OCH3), 2.56 (s, 6H, CH3).

Workup

  1. customprecipitates
  2. customwere removed by filtration
  3. washwashed several times with methanol
  4. customafter drying under reduced pressure at 65° C.

Sources & evidence

ORD record
ord-0583e585ffac4fa1a195cf71238f6023
Source dataset
uspto-grants-2013_02
Patent number
US08377895B2

Reaction notes

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