Isopropylamine → HCID 11699738, compound

HRID 1868589Notes

Reaction equation

HRID 1868589 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:28]=[C:29]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH:30]=1)[C:12]1[O:13][C:14]2[C:19]([C:20](=[O:22])[CH:21]=1)=[CH:18][CH:17]=[C:16]([O:23][CH2:24][CH:25]1[O:27][CH2:26]1)[CH:15]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:39]([NH2:42])([CH3:41])[CH3:40]>CO>[CH2:32]([O:31][C:29]1[CH:28]=[C:11]([CH:10]=[C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:30]=1)[C:12]1[O:13][C:14]2[C:19]([C:20](=[O:22])[CH:21]=1)=[CH:18][CH:17]=[C:16]([O:23][CH2:24][CH:25]([OH:27])[CH2:26][NH:42][CH:39]([CH3:41])[CH3:40])[CH:15]=2)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

4

Reactant 2

HCID 6363IsopropylamineHCID 76554795HCID 76554795, compound2×

Product 1

HCID 11699738HCID 11699738, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3′,5′-Dibenzyloxy-7-(2,3-epoxy-propoxy)-flavone, 28 (2.5 g, 4.9 mmol) and iso-propyl amine (1.8 mL, 14.7 mmol) in dry methanol (150 mL) were reacted in a similar manner to that described under 34 to afford 35. Yield 2.2 g (79%); mp 173-174° C.; MS (FAB) 566 (M++1); IR (KBr) 3431, 1637; 1H NMR (200 MHz, CDCl3) δ 8.05 (d, J=8.6 Hz, 1H), 7.59-7.34 (m, 10H), 7.15 (d, J=1.8 Hz, 2H), 7.06 (s, 1H), 7.03 (d, J=9.4 Hz, 1H), 6.78 (s, 1H), 6.71 (s, 1H), 5.13 (s, 4H), 4.14-4.11 (m, 3H), 3.18-3.16 (m, 1H), 2.93-2.79 (m, 2H), 1.11 (d, J=6.2 Hz, 6H); 13C NMR δ 177.9, 163.8, 162.9, 160.6, 158.1, 136.7, 133.9, 128.9, 128.5, 127.8, 127.1, 118.1, 115.3, 108.0, 105.8, 105.3, 101.5, 71.7, 70.7, 68.4, 49.8, 49.3, 23.1, 23.0. Analysis Calcd for C35H35NO6: C, 74.32; H, 6.24; N, 2.48. Found: C, 74.16; H, 6.17; N, 2.29.

Sources & evidence

ORD record
ord-6ee11c9082c24ec7aeb06f502a870591
Source dataset
uspto-grants-2009_12
Patent number
US07635779B2

Reaction notes

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