Formaldehyde → HCID 44608177, compound

HRID 388202Notes

Reaction equation

HRID 388202 reaction equation
[CH:1]1[CH:2]=[CH:3][C:4]([C:7]2[O:20][C:12]3=[CH:13][C:14]([OH:19])=[C:15]([OH:18])[C:16]([OH:17])=[C:11]3[C:9](=[O:10])[CH:8]=2)=[CH:5][CH:6]=1.[CH2:21]=O.[OH:23][CH:24]1[CH2:28][CH2:27][NH:26][CH2:25]1>CO>[OH:17][C:16]1[C:15]([OH:18])=[C:14]([OH:19])[C:13]([CH2:21][N:26]2[CH2:27][CH2:28][CH:24]([OH:23])[CH2:25]2)=[C:12]2[C:11]=1[C:9](=[O:10])[CH:8]=[C:7]([C:4]1[CH:3]=[CH:2][CH:1]=[CH:6][CH:5]=1)[O:20]2

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 982104-HydroxypyrrolidineHCID 5281605Baicalein

Product 1

HCID 44608177HCID 44608177, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

The mixture of Baicalein (27 g), methanol (350 ml), 37% formaldehyde solution (8.04 ml), 3-hydroxyl-pyrrolidine (8.8 g) was stirred under for 4 hours at 50° 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 36.0 g of purity 99.0%. MS: (API-ES) m/z 370.1[M+H]+, 739.2 [2M+H]+, 761.2[2M+Na]+; 1H NMR (DMSO-d6, 400 MHz): δ 8.05˜8.07 (m, 2H, Ar-2′,6′-H), 7.58˜7.59 (m, 3H, Ar-3′,4′,5′-H), 6.87 (s, 1H, 3-H), 4.17 (s, 2H, CH2), 3.32 (m, 1H, CH), 2.28, 2.53 (m, 2H, CH2), 2.20, 2.30 (m, 2H, CH2), 1.81, 1.62 (m, 2H, CH2).

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-1d70504f566f4836b43c5b65cdfbbe70
Source dataset
uspto-grants-2013_02
Patent number
US08377895B2

Reaction notes

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