Anthranilamide → 2-(4-(Dimethylamino)naphthalen-1-yl)quinazolin-4(3H)-one

HRID 555483Notes

Reaction equation

HRID 555483 reaction equation
[C:1]([NH2:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[NH2:4].[CH3:11][N:12]([CH3:25])[C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16]([CH:23]=O)=[CH:15][CH:14]=1.COC1C=C(OC)C=C2C=1C(=O)NC(C1C=CC=CN=1)=N2>>[CH3:11][N:12]([CH3:25])[C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16]([C:23]2[NH:10][C:1](=[O:9])[C:2]3[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=3)[N:4]=2)=[CH:15][CH:14]=1

Participants

4

Reactant 3

HCID 6942AnthranilamideHCID 6080524-Dimethylamino-1-naphthaldehydeHCID 1360379985,7-dimethoxy-2-(pyridin-2-yl)quinazolin-4(3H)-one

Product 1

HCID 1360379862-(4-(Dimethylamino)naphthalen-1-yl)quinazolin-4(3H)-oneYield 69%

Procedure

2-(4-(Dimethylamino)naphthalen-1-yl)quinazolin-4(3H)-one was synthesized from anthranilamide and 4-dimethylamino-naphthalene-1-carbaldehyde, using the method described for 5,7-dimethoxy-2-(pyridin-2-yl)quinazolin-4(3H)-one. 2-(4-(Dimethylamino)naphthalen-1-yl)quinazolin-4(3H)-one (240 mg, 69%) was isolated as a pale yellow solid. Selected data: MS (m/z): 316.08; MP 224-226° C.

Sources & evidence

ORD record
ord-cece9c8c08414761ad3a6070d6f2a77a
Source dataset
uspto-grants-2011_11
Patent number
US08053440B2

Reaction notes

Loading…