1,4-Anthracenedione, 2,3-dihydro-9,10-dihydroxy- → HCID 68830679, compound

HRID 226252Notes

Reaction equation

HRID 226252 reaction equation
[CH2:1]1[C:15](=O)[C:14]2[C:5](=[C:6]([OH:18])[C:7]3[C:12]([C:13]=2[OH:17])=[CH:11][CH:10]=[CH:9][CH:8]=3)[C:3](=O)[CH2:2]1.[NH2:19][CH2:20][CH2:21][N:22]1[CH2:27][CH2:26][CH2:25][CH:24]([CH2:28][OH:29])[CH2:23]1>C(O)C>[OH:29][CH2:28][CH:24]1[CH2:25][CH2:26][CH2:27][N:22]([CH2:21][CH2:20][NH:19][C:15]2[C:14]3[C:13](=[O:17])[C:12]4[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=4)[C:6](=[O:18])[C:5]=3[C:3]([NH:19][CH2:20][CH2:21][N:22]3[CH2:27][CH2:26][CH2:25][CH:24]([CH2:28][OH:29])[CH2:23]3)=[CH:2][CH:1]=2)[CH2:23]1

Participants

4

Reactant 2

HCID 872111,4-Anthracenedione, 2,3-dihydro-9,10-dihydroxy-HCID 43590171[1-(2-Aminoethyl)piperidin-3-yl]methanol

Product 1

HCID 68830679HCID 68830679, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Although not shown in scheme 3, the method follows that of HAQ70 using leucoquinizarin (0.23 g, 0.95 mmol), [1-(2-aminoethyl)-piperidin-3-yl-]methanol (0.06 g, 3.8 mmol) and ethanol (25 mL). The title compound was yielded as a dark-blue solid (0.15 g, 29%). M.p. 112-114° C.; δH(250 MHz; CDCl3); 1.15 (m, 2H, 2×CH2CHCH2OH), 1.5-1.75 (m, 6H, 2×CH2CH2CH and 2×CH2CH2CH2), 1.85 (m, 2H, 2×CH2CH2CH), 2.3 (m, 4H, 4×ring-H), 2.5 (s (broad), 4H, 2×ring-H, 2×OH), 2.65 (t, 4H, J=5 Hz, 2×HNCH2CH2N), 2.75 (2×d, 2H, J=3 Hz and 12 Hz, 2×ring-H), 3.42 (q, 4H, J=5 Hz, 2×HNCH2CH2N), 3.55 (2×d, 2H, J=5 Hz and 12 Hz, 2×CHCH2OH), 3.7 (2×d, 2H, J=9 Hz and 12 Hz, 2×CHCH2OH), 7.1 (s, 2H, C(2)H and C(3)H), 7.6 (m, 2H, C(6)H and C(7)H), 8.3 (m, 2H, C(5)H, C(8)H) and 10.75 (t, 2H, C(1)NH and C(4)NH); δC(62.9 MHz; CDCl3); 24.08, 26.92, 37.90, 40.52, 54.43, 56.95, 57.75, 65.70, 109.89, 123.87, 126.13, 132.09, 134.46, 146.6 and 182.36; FAB MS, m/z(M+H)+ 521; IR υmax/cm−1; 3400 (OH), 3090 (Ar—CH), 2960-2800 (CH2, CH3), 1650, 1585, 1550, 1520, 1265, 1175 and 1125; Anal. calcd for C30H40N4O4: C, 69.21; H, 7.74; N, 10.76. Found: C, 69.22; H, 7.88; N, 10.69.

Sources & evidence

ORD record
ord-ac9d0e540f3d46d89ecc15ace87a6c45
Source dataset
uspto-grants-2009_07
Patent number
US07557215B2

Reaction notes

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