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

HRID 1884000Notes

Reaction equation

HRID 1884000 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-69a85b4081e048ddb165f6ac6f472afb
Source dataset
uspto-grants-2004_07
Patent number
US06762188B1

Reaction notes

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