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

HRID 1654353Notes

Reaction equation

HRID 1654353 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-1899b6aed26047dcad98c43c1afcc962
Source dataset
uspto-grants-1995_04
Patent number
US05405851

Reaction notes

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