Diethanolamine → 3-[N,N-bis(2-hydroxyethyl)amino]methyl-1,8-dihydroxy-9,10-anthraquinone

HRID 344779Notes

Reaction equation

HRID 344779 reaction equation
Br[CH2:2][C:3]1[CH:4]=[C:5]([OH:20])[C:6]2[C:7](=[O:19])[C:8]3[C:13]([C:14](=[O:17])[C:15]=2[CH:16]=1)=[CH:12][CH:11]=[CH:10][C:9]=3[OH:18].[OH:21][CH2:22][CH2:23][NH:24][CH2:25][CH2:26][OH:27]>CN(C)C=O>[OH:21][CH2:22][CH2:23][N:24]([CH2:2][C:3]1[CH:4]=[C:5]([OH:20])[C:6]2[C:7](=[O:19])[C:8]3[C:13]([C:14](=[O:17])[C:15]=2[CH:16]=1)=[CH:12][CH:11]=[CH:10][C:9]=3[OH:18])[CH2:25][CH2:26][OH:27]

Participants

4

Reactant 2

HCID 8113DiethanolamineHCID 1533699,10-Anthracenedione, 3-(bromomethyl)-1,8-dihydroxy-

Product 1

HCID 1476673-[N,N-bis(2-hydroxyethyl)amino]methyl-1,8-dihydroxy-9,10-anthraquinone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-bromomethyl-1,8-dihydroxy-9,10-anthraquinone (456 mg) and bis(2-hydroxyethyl)amine (600 mg) in N,N-dimethylformamide (20 mL) is stirred for 2 hours, and then partitioned between chloroform (100 mL) and water (100 mL). The organic layer is separated, washed with water (50 mL× 3), dried over sodium sulfate, and then concentrated to dryness. The residue is chromatographed on a silica gel column using chloroform-methanol (15:1 v/v) as the eluent. Upon concentration of the major fraction, 3-[N,N-bis(2-hydroxyethyl)amino] methyl-1,8-dihydroxy-9,10-anthraquinone is obtained as a solid: 1H NMR (CDCl3)δ: 2.77 (4H, t, NCH2CH2O), 3.78 (4H, t, NCH2CH2O), 4.78 (2H, s, CH2N=), 7.21-7.29 (5H, m, aromatic H), 11.95 (1H, s, OH), 12.00 (1H, s, OH).

Workup

  1. custompartitioned between chloroform (100 mL) and water (100 mL)
  2. customThe organic layer is separated
  3. washwashed with water (50 mL× 3)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated to dryness
  6. customThe residue is chromatographed on a silica gel column

Sources & evidence

ORD record
ord-cce48f01b18b415db43884e6d253f21a
Source dataset
uspto-grants-1991_10
Patent number
US05053431

Reaction notes

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