HCID 68643698, compound → Methylamine

HRID 1157982Notes

Reaction equation

HRID 1157982 reaction equation
CO[C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][C:13]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH:23]([OH:37])[CH2:24][N:25]3CCN(C4C=CC=CC=4)C[CH2:26]3)=[CH:17][CH:16]=2)=[O:14])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]>CO>[OH:37][CH:23]([CH2:24][NH:25][CH3:26])[CH2:22][O:21][C:18]1[CH:19]=[CH:20][C:15]([C:13](=[O:14])[CH:12]=[CH:11][C:5]2[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[CH:3][CH:4]=2)=[CH:16][CH:17]=1.[O:37]1[CH2:24][CH:23]1[CH2:22][O:21][C:18]1[CH:17]=[CH:16][C:15]([C:13](=[O:14])[CH:12]=[CH:11][C:5]2[CH:4]=[CH:3][C:8]([O:9][CH3:10])=[CH:7][CH:6]=2)=[CH:20][CH:19]=1.[CH3:24][NH2:25]

Participants

5

Reactant 1

HCID 68643698HCID 68643698, compound

Product 3

HCID 6329MethylamineHCID 68643598HCID 68643598, compoundHCID 76010298HCID 76010298, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a similar manner to the preparation of 18, compound 26 was obtained from 4′-(2,3-epoxy-propoxy)-4-methoxy-chalcone, 13 (1 g, 3.2 mmol) and methylamine (5.5 mL, 64 mmol) in dry methanol (80 mL). Yield 470 mg (43%); mp 114-115° C.; MS (FAB) 342 (M++1); IR (KBr) 3487, 3344, 1652; 1H NMR (200 MHz, CDCl3) δ 8.01 (d, J=8.6 Hz, 2H), 7.77 (d, J=15.6 Hz, 1H), 7.59 (d, J=8.5 Hz, 2H), 7.41 (d, J=15.6 Hz, 1H), 6.98 (d, J=8.9 Hz, 2H), 6.93 (d, J=8.7 Hz, 2H), 4.07-4.05 (m, 3H), 3.85 (s, 3H), 2.93-2.82 (m, 2H), 2.50 (s, 3H). Analyses calculated for C20H23NO4: C, 70.36; H, 6.79; N, 4.10. Found: C, 70.40; H, 6.72; N, 4.13.

Sources & evidence

ORD record
ord-1785f7bd8b5a42dc9f643dc52d15e41f
Source dataset
uspto-grants-2010_10
Patent number
US07807712B2

Reaction notes

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