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

HRID 381558Notes

Reaction equation

HRID 381558 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-d, 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-cb0c0a95048e4664bcb4a5ee31aab441
Source dataset
uspto-grants-2001_10
Patent number
US06306865B1

Reaction notes

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