Morpholine → 2-Benzyloxy-6-(morpholin-4-yl)-benzo[de]isoquinoline-1,3-dione

HRID 567009Notes

Reaction equation

HRID 567009 reaction equation
[CH2:1]([O:8][N:9]1[C:18](=[O:19])[C:17]2[CH:20]=[CH:21][C:22](Br)=[C:15]3[C:16]=2[C:11](=[CH:12][CH:13]=[CH:14]3)[C:10]1=[O:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1CCN2C(=NCCC2)CC1.[NH:36]1[CH2:41][CH2:40][O:39][CH2:38][CH2:37]1>>[CH2:1]([O:8][N:9]1[C:18](=[O:19])[C:17]2[CH:20]=[CH:21][C:22]([N:36]3[CH2:41][CH2:40][O:39][CH2:38][CH2:37]3)=[C:15]3[C:16]=2[C:11](=[CH:12][CH:13]=[CH:14]3)[C:10]1=[O:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 8083MorpholineHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 226240382-Benzyloxy-6-bromo-benzo[de]isoquinoline-1,3-dione

Product 1

HCID 226239062-Benzyloxy-6-(morpholin-4-yl)-benzo[de]isoquinoline-1,3-dione

Procedure

2-Benzyloxy-6-bromo-benzo[de]isoquinoline-1,3-dione (0.8 g, 2.1 mmol, from Example M) was reacted in morpholine (3.0 mL) in the presence of DBU (0.05 mL) following the procedure of Example 18 to give 0.6 g of 2-benzyloxy-6-(morpholin-4-yl)-benzo[de]isoquinoline-1,3-dione. Hydrogenation of 2-benzyloxy-6-(morpholin-4-yl)-benzo[de]isoquinoline-1,3-dione (0.4 g, 0.9 mmol) in the presence of 10% Pd/C (0.2 g) in DMA (30 mL) afforded 0.2 g of the title compound, mp 235-237° C.; 1H NMR (DMSO-d6): δ 10.6 (1H, s), 8.5-8.4 (3H, m), 7.8 (1H, t, J=7.9), 7.4 (1H, d, J=8.1), 3.9 (4H, m), 3.2 (4H, m).

Sources & evidence

ORD record
ord-ae26668f7cdc4cde90d9574e135f9a1d
Source dataset
uspto-grants-2001_01
Patent number
US06177423B1

Reaction notes

Loading…