Guanidine → 5,6-dihydro-3-(methylamino)benzo[f]quinazolin-1(2H)-one

HRID 2289244Notes

Reaction equation

HRID 2289244 reaction equation
O[C:2]1[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]=1[C:12]([O:14]C)=O.[CH3:16][NH:17][C:18]([NH2:20])=[NH:19].NC(N)=N>>[CH3:16][NH:17][C:18]1[NH:20][C:12](=[O:14])[C:3]2[C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:9]=3[CH2:10][CH2:11][C:2]=2[N:19]=1

Participants

4

Reactant 3

HCID 3520GuanidineHCID 546921643,4-Dihydro-2-hydroxynaphthalenecarboxylic Acid, Methyl EsterHCID 178485088HCID 178485088, compound

Product 1

HCID 1358381435,6-dihydro-3-(methylamino)benzo[f]quinazolin-1(2H)-one

Procedure

Methyl 3,4-dihydro-2-hydroxy-1-naphthoate was reacted with methyl- guanidine in the same manner as for the analogous reaction using guanidine (example 1) to obtain 5,6-dihydro-3-(methylamino)benzo[f]quinazolin-1(2H)-one. 1H NMR(DMSO-d61 200 MHz) δ: 2.52-2.64(m, 2.H, CH2), 2.68-2.82(m, 2H, CH2), 2.81(d, J=5 Hz, 3H, NCH3), 6.54(br s, 1H, C3NH), 7.02 (ddd, J=8, 8, 2 Hz, 1H, Ar), 7.07-7.18(m, 2H, Ar), 8.42(dd, J=8,2 Hz, 1H, Ar), 10.98(br s, 1H, N 2H).

Sources & evidence

ORD record
ord-5f141305809441fe9d9941b15eecda3a
Source dataset
uspto-grants-2000_07
Patent number
US06090941

Reaction notes

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