Triethylamine → (4E)-4-(methoxymethylene)isoquinoline-1,3(2H,4H)-dione

HRID 2236614Notes

Reaction equation

HRID 2236614 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][C:6](=[O:13])/[C:5]/2=[CH:14]\NCC1C=CC(O)=C(OC)C=1.Cl.[OH:27][C:28]1C=C(C=CC=1)CN.C(N(CC)CC)C>>[CH3:28][O:27]/[CH:14]=[C:5]1/[C:6](=[O:13])[NH:7][C:8](=[O:12])[C:9]2[C:4]/1=[CH:3][CH:2]=[CH:11][CH:10]=2

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 220584273-(Aminomethyl)phenol hydrochlorideHCID 178492243HCID 178492243, compound

Product 1

HCID 59300321(4E)-4-(methoxymethylene)isoquinoline-1,3(2H,4H)-dione

Procedure

Using the procedure described for the preparation of (4Z)-6-bromo-4-{[(4-hydroxy-3-methoxybenzyl)amino]methylene}isoquinoline-1,3(2H,4H)-dione, 0.25 g (78% yield) of off-white solid is obtained from 0.2 g (0.98 mmol) of (4E)-4-(methoxymethylene)-isoquinoline-1,3(2H,4H)-dione and 0.2 g (1.08 mmol) of 4-methoxy]-3-hydroxyl-benzylamine hydrochloride, and 0.3 mL (2.94 mmol) of triethylamine: mp 192-193° C.; 1H NMR (DMSO-d6) δ 10.97 (s, 1H), 10.60 (m, 1H), 9.04 (s, 1H), 8.62 (d, J=9 Hz, 1H), 7.98 (d, J=6 Hz, 1H), 7.83 (d, J=6 Hz, 1H), 7.55 (t, J=6 Hz, 1H), 7.17 (t, J=6 Hz, 1H), 6.91 (d, J=6 Hz, 1H), 6.78 (m, 2H), 4.56 (d, J=4.5 Hz, 2H), 3.75 (s, 3H); MS (ESI) m/z 325.1 (M+H)+1.

Sources & evidence

ORD record
ord-96fe45c1a79d4ef59cc02321f158d5da
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

Loading…