Guanidine → 3-amino-8-bromo-5,6-dihydrobenzo[f]quinazolin-1(2H)-one

HRID 2258659Notes

Reaction equation

HRID 2258659 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([C:12]([O:14]CC)=O)=[C:7](O)[CH2:6][CH2:5]2.[NH2:18][C:19]([NH2:21])=[NH:20]>>[NH2:20][C:19]1[NH:21][C:12](=[O:14])[C:8]2[C:9]3[CH:10]=[CH:11][C:2]([Br:1])=[CH:3][C:4]=3[CH2:5][CH2:6][C:7]=2[N:18]=1

Participants

3

Reactant 2

HCID 3520GuanidineHCID 54708333Ethyl 6-bromo-3,4-dihydro-2-hydroxy-1-naphthoate

Product 1

HCID 1358381833-amino-8-bromo-5,6-dihydrobenzo[f]quinazolin-1(2H)-one

Procedure

Ethyl 6-bromo-3,4-dihydro-2-hydroxy-1-naphthoate (6.0 g, 20.2 mmoles) was reacted with guanidine (6.9 g of hydrochloride salt, 72.2 mmoles) in the same manner as in example 1. The product was precipitated from aqueous sodium hydroxide with acetic acid, filtered, washed with water and dried to give 3-amino-8-bromo-5,6-dihydrobenzo[f]quinazolin-1(2H)-one as an off-white solid. (2.75 g, 46%) 1H NMR(DMSO-d6, 300 MHz) δ: 2.55(t, J=7.5 Hz, 2H, CH2); 2.79(t, J=7.4 Hz, 2H, CH2); 6.75(br s, 2H, NH2); 7.32(dd, J=8.4, 2.3 Hz, 1H, Ar); 7.34(s, 1H, Ar); 8.40(d, J=8.4 Hz, 1H, Ar); 11.00(br s, 1H, NH).

Workup

  1. customThe product was precipitated from aqueous sodium hydroxide with acetic acid
  2. filtrationfiltered
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-4e81c71b5bc24633a7272d5937735e69
Source dataset
uspto-grants-1997_08
Patent number
US05661155

Reaction notes

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