Isopropylamine → HCID 11611332, compound

HRID 1868600Notes

Reaction equation

HRID 1868600 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:22]=[CH:23][C:24]=1[O:25][CH3:26])[C:6]1[O:7][C:8]2[C:13]([C:14](=[O:16])[CH:15]=1)=[CH:12][CH:11]=[C:10]([O:17][CH2:18][CH:19]1[O:21][CH2:20]1)[CH:9]=2.[CH:27]([NH2:30])([CH3:29])[CH3:28]>CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:22]=[CH:23][C:24]=1[O:25][CH3:26])[C:6]1[O:7][C:8]2[C:13]([C:14](=[O:16])[CH:15]=1)=[CH:12][CH:11]=[C:10]([O:17][CH2:18][CH:19]([OH:21])[CH2:20][NH:30][CH:27]([CH3:29])[CH3:28])[CH:9]=2

Participants

4

Reactant 2

HCID 6363IsopropylamineHCID 86236611HCID 86236611, compound2×

Product 1

HCID 11611332HCID 11611332, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3′,4′-Dimethoxy-7-(2,3-epoxy-propoxy)-flavone, 33 (300 mg, 0.85 mmol) and iso-propyl amine (0.15 mL, 1.7 mmol) in dry methanol (80 mL) were reacted in a similar manner to that described under 34 to afford 46. Yield 290 mg (83%); mp 144-145° C.; MS (FAB) 414 (M++1); IR (KBr) 3410, 1634; 1H NMR (200 MHz, CDCl3) δ 8.03 (d, J=9.5 Hz, 1H), 7.51 (dd, J=8.5 Hz, 1.7 Hz, 1H), 7.36 (d, J=1.7 Hz, 1H), 6.96-6.92 (m, 3H), 6.74 (s, 1H), 4.18-4.12 (m, 3H), 3.97 (s, 3H), 3.96 (s, 3H), 3.99 (s, (m, 3H), 1.23 (d, J=6.3 Hz, 6H). Analysis Calcd for C23H27NO6: C, 66.81; H, 6.58; N, 3.39. Found: C, 66.67; H, 6.65; N, 3.53.

Sources & evidence

ORD record
ord-9a9792db907d4de1a4a06f9ca8985007
Source dataset
uspto-grants-2009_12
Patent number
US07635779B2

Reaction notes

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