Water → N-(3-hydroxypropyl)-2-anthraquinonecarboxamide

HRID 1860959Notes

Reaction equation

HRID 1860959 reaction equation
[CH:1]1[C:14]2[C:13](=[O:15])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6](=[O:16])[C:5]=2[CH:4]=[CH:3][C:2]=1[C:17]([OH:19])=O.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.[NH2:47][CH2:48][CH2:49][CH2:50][OH:51].O>CN(C=O)C>[OH:51][CH2:50][CH2:49][CH2:48][NH:47][C:17]([C:2]1[CH:3]=[CH:4][C:5]2[C:6](=[O:16])[C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[C:13](=[O:15])[C:14]=2[CH:1]=1)=[O:19]

Participants

6

Reactant 4

HCID 962WaterHCID 90863-Amino-1-propanolHCID 670302-Anthraquinonecarboxylic acidHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate

Product 1

HCID 18624454N-(3-hydroxypropyl)-2-anthraquinonecarboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred suspension of anthraquinone-2-carboxylic acid (Aldrich, 10.00 g, 39.64 mmol) in DMF (130 ml), was added (benzotriazol-1-yloxy)tris(dimethylamino)-phosphonium hexafluorophosphate (17.54 g, 39.66 mmol) and trethylamine (11.05 ml, 79.28 mmol). The resulting mixture (initially a clear green solution) was stirred at room temperature for 10 min. before dropwise addition of 3-amino-1-propanol (3.34 ml, 43.67 mmol). The reaction mixture (clear brown solution) was stirred at room temperature in the dark for 17 hours. The solution was poured in a thin stream into water (300 ml) containing some ice. The precipitated material was isolated by filtration and recrystallised from boiling 96% ethanol (ca. 200 ml) and gave the title compound 2 as a bright yew solid (6.93 g, 57% yield).

Workup

  1. additioncontaining some ice
  2. customThe precipitated material was isolated by filtration
  3. customrecrystallised

Sources & evidence

ORD record
ord-a3596a390b864b3884802aa695058453
Source dataset
uspto-grants-2003_03
Patent number
US06531591B1

Reaction notes

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