2,3-Dihydro-1,4-benzodioxin-6-carbaldehyde → HCID 136037972, compound

HRID 336689Notes

Reaction equation

HRID 336689 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[C:7]([O:13][CH3:14])[C:3]=1[C:4]([NH2:6])=[O:5].[O:15]1[C:20]2[CH:21]=[CH:22][C:23]([CH:25]=O)=[CH:24][C:19]=2[O:18][CH2:17][CH2:16]1.COC1C=C(OC)C=C2C=1C(=O)NC(C1C=CC=CN=1)=N2>>[O:15]1[CH2:16][CH2:17][O:18][C:19]2[CH:24]=[C:23]([C:25]3[NH:6][C:4](=[O:5])[C:3]4[C:2](=[CH:10][C:9]([O:11][CH3:12])=[CH:8][C:7]=4[O:13][CH3:14])[N:1]=3)[CH:22]=[CH:21][C:20]1=2

Participants

4

Reactant 3

HCID 2481272,3-Dihydro-1,4-benzodioxin-6-carbaldehydeHCID 203490162-Amino-4,6-dimethoxybenzamideHCID 1360379985,7-dimethoxy-2-(pyridin-2-yl)quinazolin-4(3H)-one

Product 1

HCID 136037972HCID 136037972, compoundYield 46%

Procedure

2-(2,3-Dihydrobenzo[b][1,4]dioxin-6-yl)-5,7-dimethoxyquinazolin-4(3H)-one was synthesized from 2-amino-4,6-dimethoxybenzamide and 2,3-dihydro-benzo[1,4]dioxine-6-carbaldehyde, using the method described for 5,7-dimethoxy-2-(pyridin-2-yl)quinazolin-4(3H)-one. 2-(2,3-Dihydrobenzo[b][1,4]dioxin-6-yl)-5,7-dimethoxyquinazolin-4(3H)-one (120 mg, 46%) was isolated as a yellow solid. Selected data: MS (m/z): 341.03; MP 307.5-309.6° C.

Sources & evidence

ORD record
ord-cb2610ccc504414f8b59dd0df6ece00f
Source dataset
uspto-grants-2014_11
Patent number
US08889698B2

Reaction notes

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