Bromomethyl 4-methoxyphenyl ketone → HCID 11108777, compound

HRID 1422092Notes

Reaction equation

HRID 1422092 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([CH2:9][CH2:10][CH3:11])[CH:4]=1.[CH3:12][O:13][C:14]1[CH:23]=[CH:22][C:17]([C:18](=O)[CH2:19]Br)=[CH:16][CH:15]=1>>[CH2:10]([C:9]1[C:18]([C:17]2[CH:22]=[CH:23][C:14]([O:13][CH3:12])=[CH:15][CH:16]=2)=[CH:19][N:6]2[C:5]=1[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=[CH:7]2)[CH3:11]

Participants

3

Reactant 2

HCID 4965Bromomethyl 4-methoxyphenyl ketoneHCID 110840544-Methoxy-2-n-propylpyridine

Product 1

HCID 11108777HCID 11108777, compoundYield 86%

Procedure

4-Methoxy-2-n-propylpyridine was reacted with 4-methoxyphenacylbromide by the general synthetic principle outlined in example 23, step 5, to afford 1-ethyl-7-methoxy-2-(4-methoxyphenyl)indolizine in 86% yield. M.p. 101-103° C. 1H-NMR (DMSO-d6, 200 MHz) δ: 1.10 (t, 3H); 2.77 (q, 2H); 3.77 (s, 3H); 3.80 (s, 3H); 6.23 (dd, 1H); 6.65 (d, 1H); 7.00 (d, 2H); 7.35 (s, 1H); 7.38 (d, 2H); 8.06 (d, 1H). Analysis: Calculated for C18H19N1O2 : C, 76.84; H, 6.81; N, 4.98%. Found: C, 76.73; H, 6.94; N, 4.80%.

Sources & evidence

ORD record
ord-ad5ade2e368a4cccbddc94bd65f0f023
Source dataset
uspto-grants-2000_06
Patent number
US06080754

Reaction notes

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