Anthranilamide → 2-(2,3-Dihydrobenzo[b][1,4]dioxin-6-yl)quinazolin-4(3H)-one

HRID 555479Notes

Reaction equation

HRID 555479 reaction equation
[C:1]([NH2:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[NH2:4].N1C=CC=N[C:12]=1[O:17][C:18]1[CH:25]=[CH:24][C:21]([CH:22]=O)=[CH:20][CH:19]=1.[CH3:26][O:27]C1C=C(OC)C=C2C=1C(=O)NC(C1C=CC=CN=1)=N2>>[O:17]1[CH2:12][CH2:26][O:27][C:25]2[CH:24]=[C:21]([C:22]3[NH:10][C:1](=[O:9])[C:2]4[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=4)[N:4]=3)[CH:20]=[CH:19][C:18]1=2

Participants

4

Reactant 3

HCID 6942AnthranilamideHCID 27635624-(Pyrimidin-2-yloxy)benzaldehydeHCID 1360379985,7-dimethoxy-2-(pyridin-2-yl)quinazolin-4(3H)-one

Product 1

HCID 1360380202-(2,3-Dihydrobenzo[b][1,4]dioxin-6-yl)quinazolin-4(3H)-oneYield 72%

Procedure

2-(2,3-Dihydrobenzo[b][1,4]dioxin-6-yl)quinazolin-4(3H)-one was synthesized from anthranilamide and 4-(pyrimidin-2-yloxy)-benzaldehyde, 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)quinazolin-4(3H)-one (222 mg, 72%) was isolated as a light beige solid. Selected data: MS (m/z): 280.98; MP 267-268° C. (decomposed).

Sources & evidence

ORD record
ord-22ddd056d10f4aab90789f4a852aa7f5
Source dataset
uspto-grants-2011_11
Patent number
US08053440B2

Reaction notes

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